Resin composition

Abstract

[Problem] To provide a resin composition with which it is possible to obtain a cured product having good mechanical properties while exhibiting good dielectric properties, and particularly having high elongation at break and excellent crack resistance. [Solution] A resin composition containing the following component (A), component (B), and component (C): (A) a compound represented by formula (A-1): [Chemical Formula 1] # imgabs0 # (in formula (A-1), X represents a specific divalent group); (B) a maleimide resin; and (C) a thermosetting resin (excluding a maleimide resin).

Description

Technical Field

[0001] The present invention relates to a resin composition, a cured product obtained by using the resin composition, a resin sheet, a circuit board, and a semiconductor device. Background Art

[0002] An insulating layer is provided on a circuit board such as a printed wiring board or a rewiring board of a semiconductor chip package. Generally, the insulating layer is formed by curing a resin composition. As the insulating layer of the circuit board, in order to suppress transmission loss when operating in a high-frequency environment, it is required to exhibit good dielectric properties (low dielectric constant, low dielectric loss tangent).

[0003] As a resin material that gives a cured product having good dielectric properties, for example, a resin composition containing a maleimide resin has been reported (Patent Document 1).

[0004] Prior Art Documents

[0005] Patent Documents

[0006] Patent Document 1: Japanese Unexamined Patent Application Publication No. 2012-116941 Summary of the Invention

[0007] Problems to be Solved by the Invention

[0008] As disclosed in Patent Document 1, a resin composition containing a maleimide resin generally gives a cured product having good dielectric properties. On the other hand, it tends to be prone to cracking after a defouling treatment. In addition, maleimide resins generally have a high softening point, so the cured product of a resin composition containing a maleimide resin is brittle and tends to have poor mechanical properties.

[0009] An object of the present invention is to provide a resin composition, a cured product obtained by using the resin composition, a resin sheet containing the resin composition, a circuit board, and a semiconductor device, wherein the resin composition can obtain a cured product that exhibits good dielectric properties and at the same time exhibits good mechanical properties, specifically, has a high elongation at break (elongation at the breaking point) and excellent crack resistance.

[0010] Means for Solving the Problems

[0011] The present inventors conducted intensive studies to solve the above problems. As a result, the present inventors found that a resin composition containing a compound having a specific structure combined with a maleimide resin and a thermosetting resin other than the maleimide resin can solve the above problems, and thus completed the present invention.

[0012] That is, the present invention includes the following contents.

[0013] [1]A resin composition containing the following components (A), (B), and (C).

[0014] (A) A compound represented by the following formula (A-1):

[0015] [Chemical formula 1]

[0016]

[0017] (In formula (A-1), X represents a divalent group represented by the following formula (A-2) or a divalent group represented by the following formula (A-3).)

[0018] [Chemical formula 2]

[0019]

[0020] (In formula (A-2),

[0021] R 11 and R 12 each independently represent a divalent aromatic group optionally having a substituent,

[0022] L 11 each independently represent a single bond or a divalent linking group optionally having a substituent,

[0023] R 11 and L 11 may combine together to form a ring.

[0024] a represents a number in the range of 0 to 5.)

[0025] [Chemical formula 3]

[0026]

[0027] (In formula (A-3),

[0028] R 13 and R 14 each independently represent a divalent aromatic group optionally having a substituent,

[0029] L 12 represents a group represented by formula (A-4).

[0030] b and c each independently represent a number in the range of 0 to 5.)

[0031] [Chemical formula 4]

[0032]

[0033] (In formula (A-4),

[0034] R15 and R 16 each independently represents an optionally substituted divalent aromatic group,

[0035] L 13 each independently represents a single bond, or an optionally substituted divalent linking group,

[0036] R 15 and L 13 may combine together to form a ring.

[0037] d represents a number in the range of 0 to 5.);

[0038] (B) a maleimide resin;

[0039] (C) a thermosetting resin (excluding the maleimide resin).

[0040] [2] The resin composition according to [1], wherein R in formula (A-2) and formula (A-3) 11 、R 12 、R 13 and R 14 each independently represents an optionally substituted phenylene group or an optionally substituted naphthylene group.

[0041] [3] The resin composition according to [1] or [2], wherein R in formula (A-4) 15 and R 16 each independently represents an optionally substituted phenylene group or an optionally substituted naphthylene group.

[0042] [4] The resin composition according to any one of [1] to [3], wherein L in formula (A-2) 11 each independently represents a single bond, an optionally substituted divalent aliphatic group, an oxygen atom, an optionally substituted divalent aromatic group, a carbonyl group, and a sulfonyl group.

[0043] [5] The resin composition according to any one of [1] to [4], wherein L in formula (A-2) 11 each independently represents a single bond, an optionally substituted divalent aliphatic group, an oxygen atom, a phenylene group, a fluorene group, a carbonyl group, or a sulfonyl group.

[0044] [6] The resin composition according to any one of [1] to [5], wherein X in formula (A-1) is a group represented by the following formula (A-5),

[0045] [Chemical formula 5]

[0046]

[0047] (In formula (A-5),

[0048] Each Rs independently represents a substituent,

[0049] L 21 Each independently represents a single bond, a divalent aliphatic group optionally having a substituent, an oxygen atom, a phenylene group, a fluorene-9,9-diyl group, a carbonyl group, or a sulfonyl group. When L 21 is a divalent aliphatic group optionally having a substituent, L 21 may combine with the benzene ring on the left to form a ring,

[0050] n1 and n2 each independently represent a number in the range of 0 to 4,

[0051] m represents a number in the range of 0 to 5,

[0052] “*” represents a linking bond.).

[0053] [7] The resin composition according to any one of [1] to [6], wherein when the resin component in the resin composition is set to 100% by mass, the content of the component (A) is 2% by mass or more and 12% by mass or less.

[0054] [8] The resin composition according to any one of [1] to [7], wherein when the resin component in the resin composition is set to 100% by mass, the content of the component (B) is 20% by mass or more and 75% by mass or less.

[0055] [9] The resin composition according to any one of [1] to [8], wherein the component (C) contains one or more selected from epoxy resins, phenolic resins, and terminal double bond resins.

[0056]

[10] The resin composition according to any one of [1] to [9], wherein when the resin component in the resin composition is set to 100% by mass, the thermosetting resin (C) is 10% by mass or more and 50% by mass or less.

[0057]

[11] The resin composition according to any one of [1] to

[10] , further containing a (D) thermoplastic resin.

[0058]

[12] The resin composition according to any one of [1] to

[11] , further containing an (E) inorganic filler.

[0059]

[13] The resin composition according to

[12] , wherein when the non-volatile component in the resin composition is set to 100% by mass, the content of the component (E) is 50% by mass or more.

[0060]

[14] The resin composition according to any one of [1] to

[13] is used for an insulating layer of a circuit board.

[0061]

[15] A cured product which is a cured product of the resin composition according to any one of [1] to

[13] .

[0062]

[16] A resin sheet which includes a support and a layer of the resin composition according to any one of [1] to

[13] provided on the support.

[0063]

[17] The resin sheet according to

[16] , wherein the support is a thermoplastic resin film or a metal foil.

[0064]

[18] A circuit board which includes an insulating layer formed of a cured product of the resin composition according to any one of [1] to

[13] .

[0065]

[19] A semiconductor device which includes the circuit board according to

[18] .

[0066] Effects of the Invention

[0067] According to the resin composition of the present invention, a resin composition, a cured product, a resin sheet, a circuit board, and a semiconductor device obtained by using the resin composition can be provided. The resin composition can obtain a cured product that exhibits good dielectric properties and at the same time exhibits good mechanical properties, specifically, a high elongation at break and excellent crack resistance. Detailed Embodiments

[0068] Hereinafter, embodiments and exemplifications of the present invention will be described. However, the present invention is not limited to the embodiments and exemplifications shown below, and can be arbitrarily modified and implemented without departing from the scope of the claims and their equivalents.

[0069] In this specification, the term "optionally having a substituent" for a compound or a group means both the case where a hydrogen atom of the compound or the group is not substituted by a substituent and the case where a part or all of the hydrogen atoms of the compound or the group are substituted by a substituent.

[0070] In this specification, unless otherwise specified, the "substituent" means a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, a cycloalkyloxy group, an aryl group, an aryloxy group, an arylalkyl group, an arylalkoxy group, a monovalent heterocyclic group, an alkylidene group, an amino group, a silyl group, an acyl group, an acyloxy group, a carboxyl group, a sulfo group, a cyano group, a nitro group, a hydroxyl group, a mercapto group, and an oxo group.

[0071] Examples of the halogen atom used as a substituent include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0072] The alkyl group used as a substituent can be either straight-chain or branched-chain. The number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 14, further preferably 1 to 12, still further preferably 1 to 6, and particularly preferably 1 to 3. Examples of the alkyl group include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0073] The number of carbon atoms of the cycloalkyl group used as a substituent is preferably 3 to 20, more preferably 3 to 12, and further preferably 3 to 6. Examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0074] The alkoxy group used as a substituent can be either straight-chain or branched-chain. The number of carbon atoms of the alkoxy group is preferably 1 to 20, more preferably 1 to 12, and further preferably 1 to 6. Examples of the alkoxy group include methoxy, ethoxy, propyloxy, isopropyloxy, butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, and decyloxy.

[0075] The alkenyl group used as a substituent is a monovalent unsaturated hydrocarbon group having one carbon-carbon double bond, and can be either straight-chain or branched-chain. The number of carbon atoms of the alkenyl group is preferably 2 to 20, more preferably 2 to 12, and further preferably 2 to 6. Examples of the alkenyl group include vinyl, allyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, and decenyl.

[0076] The number of carbon atoms of the cycloalkyloxy group used as a substituent is preferably 3 to 20, more preferably 3 to 12, and further preferably 3 to 6. Examples of the cycloalkyloxy group include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, and cyclohexyloxy.

[0077] The aryl group used as a substituent is a group obtained by removing one hydrogen atom from an aromatic ring of an aromatic hydrocarbon. The number of carbon atoms of the aryl group used as a substituent is preferably 6 to 24, more preferably 6 to 18, further preferably 6 to 14, and still further preferably 6 to 10. Examples of the aryl group include phenyl, naphthyl, and anthryl.

[0078] The number of carbon atoms of the aryloxy group used as a substituent is preferably 6 to 24, more preferably 6 to 18, further preferably 6 to 14, and still further preferably 6 to 10. Examples of the aryloxy group used as a substituent include phenoxy, 1-naphthyloxy, and 2-naphthyloxy.

[0079] The number of carbon atoms of the arylalkyl used as a substituent is preferably from 7 to 25, more preferably from 7 to 19, still more preferably from 7 to 15, and even more preferably from 7 to 11. Examples of the arylalkyl include phenyl-C 1 -C 12 alkyl, naphthyl-C 1 -C 12 alkyl, and anthryl-C 1 -C 12 alkyl.

[0080] The number of carbon atoms of the arylalkoxy used as a substituent is preferably from 7 to 25, more preferably from 7 to 19, still more preferably from 7 to 15, and even more preferably from 7 to 11. Examples of the arylalkoxy include phenyl-C 1 -C 12 alkoxy, and naphthyl-C 1 -C 12 alkoxy.

[0081] The monovalent heterocyclic group used as a substituent means a group obtained by removing one hydrogen atom from a heterocycle of a heterocyclic compound. The number of carbon atoms of the monovalent heterocyclic group is preferably from 3 to 21, more preferably from 3 to 15, still more preferably from 3 to 9. The monovalent heterocyclic group also includes a monovalent aromatic heterocyclic group (heteroaryl). Examples of the monovalent heterocycle include thienyl, pyrrolyl, furanyl, furyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, pyrrolidinyl, piperidinyl, quinolinyl, and isoquinolinyl.

[0082] The alkylidene used as a substituent means a group obtained by removing two hydrogen atoms from the same carbon atoms of an alkane. The number of carbon atoms of the alkylidene is preferably from 1 to 20, more preferably from 1 to 14, still more preferably from 1 to 12, even more preferably from 1 to 6, and particularly preferably from 1 to 3. Examples of the alkylidene include methylidene, ethylidene, propylidene, isopropylidene, butylidene, sec-butylidene, isobutylidene, tert-butylidene, pentylidene, hexylidene, heptylidene, octylidene, nonylidene, and decylidene.

[0083] The acyl group used as a substituent means a group represented by the formula: -C(=O)-R (wherein R is an alkyl group or an aryl group). The alkyl group represented by R may be either linear or branched. Examples of the aryl group represented by R include phenyl, naphthyl, and anthryl. The number of carbon atoms of the acyl group is preferably from 2 to 20, more preferably from 2 to 13, still more preferably from 2 to 7. Examples of the acyl group include acetyl, propionyl, butyryl, isobutyryl, pivaloyl, and benzoyl.

[0084] The acyloxy group used as a substituent refers to a group represented by the formula: -O-C(=O)-R (wherein R is an alkyl group or an aryl group). The alkyl group represented by R can be either linear or branched. Examples of the aryl group represented by R include a phenyl group, a naphthyl group, and an anthracenyl group. The number of carbon atoms of the acyloxy group is preferably 2 to 20, more preferably 2 to 13, and still more preferably 2 to 7. Examples of the acyloxy group include an acetoxy group, a propionyloxy group, a butyryloxy group, an isobutyryloxy group, a pivaloyloxy group, and a benzoyloxy group.

[0085] The above-mentioned substituent may optionally further have a substituent (hereinafter sometimes referred to as a "secondary substituent"). As the secondary substituent, the same groups as those of the above-mentioned substituent can be used as long as there is no particular description.

[0086] In the present specification, the term "aromatic ring" refers to a ring that follows Hückel's rule and has 4p + 2 electrons (where p is a natural number) in the π electron system of the ring. The aromatic ring can be an aromatic carbocyclic ring having only carbon atoms as ring-forming atoms, or an aromatic heterocyclic ring having, in addition to carbon atoms, heteroatoms such as oxygen atoms, nitrogen atoms, and sulfur atoms as ring-forming atoms. The aromatic ring is preferably an aromatic carbocyclic ring. In addition, the aromatic ring such as an aromatic carbocyclic ring is preferably a 5- to 14-membered aromatic ring, more preferably a 6- to 14-membered aromatic ring, and still more preferably a 6- to 10-membered aromatic ring. Suitable specific examples of the aromatic carbocyclic ring include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring, more preferably a benzene ring or a naphthalene ring, and particularly preferably a benzene ring.

[0087] In the present specification, the term "non-aromatic ring" refers to a ring other than an aromatic ring having aromaticity as a whole ring. The non-aromatic ring may be a non-aromatic carbocyclic ring having only carbon atoms as ring-forming atoms, or a non-aromatic heterocyclic ring having, in addition to carbon atoms, heteroatoms such as oxygen atoms, nitrogen atoms, and sulfur atoms as ring-forming atoms. The non-aromatic ring is preferably a non-aromatic carbocyclic ring. The non-aromatic ring may be a saturated ring or an unsaturated ring. The non-aromatic ring is preferably a non-aromatic ring having 3 to 21 members, more preferably a non-aromatic ring having 4 to 17 members, and still more preferably a non-aromatic ring having 5 to 14 members. As suitable specific examples of the non-aromatic ring (non-aromatic carbocyclic ring), there may be mentioned monocyclic non-aromatic saturated carbocyclic rings such as cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclooctane ring; monocyclic non-aromatic unsaturated carbocyclic rings such as cyclobutene ring, cyclopentene ring, cyclohexene ring, cycloheptene ring, cyclooctene ring, cyclopentadiene ring, cyclohexadiene ring; bicyclic or higher non-aromatic saturated carbocyclic rings such as bicyclo[2.2.1]heptane ring (norbornane ring), bicyclo[4.4.0]decane ring (decalin ring), bicyclo[5.3.0]decane ring, bicyclo[4.3.0]nonane ring (hexahydroindane ring), bicyclo[3.2.1]octane ring, bicyclo[5.4.0]undecane ring, bicyclo[3.3.0]octane ring, bicyclo[3.3.1]nonane ring, tricyclo[5.2.1.0 2,6 decane ring (tetrahydrodicyclopentadiene ring), tricyclo[3.3.1.1 3,7 decane ring (adamantane ring), tricyclo[6.2.1.0 2,7 undecane ring and other bicyclic or higher non-aromatic saturated carbocyclic rings; bicyclic or higher non-aromatic unsaturated carbocyclic rings such as bicyclo[2.2.1]hept-2-ene ring (norbornene ring), bicyclo[2.2.2]oct-2-ene ring, bicyclo[4.4.0]dec-2-ene ring, etc. The non-aromatic ring may be a non-aromatic ring obtained by fusing an aromatic ring in a part thereof. As the non-aromatic ring obtained by fusing an aromatic ring in a part thereof, there may be mentioned indane ring, indene ring, tetrahydronaphthalene ring, 1,2-dihydronaphthalene ring, 1,4-dihydronaphthalene ring, fluorene ring, 9,10-dihydroanthracene ring, 9,10-dihydrophenanthrene ring, etc.

[0088] [Resin composition]

[0089] The resin composition of the present invention contains (A) a compound represented by the following formula (A-1), (B) a maleimide resin, and (C) a thermosetting resin (excluding the maleimide resin). In the present invention, by using the specific compound represented by the formula (A-1) in combination with the maleimide resin, a cured product excellent in crack resistance after a decontamination treatment can be obtained, and further, by containing a thermosetting resin (excluding the maleimide resin), a cured product exhibiting good mechanical properties, specifically, a high elongation at break can be obtained.

[0090] In addition to the above components (A) to (C), the resin composition may further contain optional components. Examples of the optional components include (D) a thermoplastic resin, (E) an inorganic filler, (F) a radical reaction initiator, (G) a curing accelerator, and other additives. Hereinafter, each component contained in the resin composition will be described in detail.

[0091] [Compound represented by formula (A-1)]

[0092] The resin composition of the present invention contains a compound represented by the following formula (A-1) as component (A):

[0093] [Chemical formula 6]

[0094]

[0095] (In formula (A-1), X represents a divalent group represented by the following formula (A-2) or a divalent group represented by the following formula (A-3).)

[0096] [Chemical formula 7]

[0097]

[0098] (In formula (A-2),

[0099] R 11 and R 12 each independently represent a divalent aromatic group optionally having a substituent,

[0100] L 11 each independently represent a single bond or a divalent linking group optionally having a substituent,

[0101] R 11 and L 11 may combine together to form a ring.

[0102] a represents a number in the range of 0 to 5.)

[0103] [Chemical formula 8]

[0104]

[0105] (In formula (A-3),

[0106] R 13 and R 14 each independently represent a divalent aromatic group optionally having a substituent,

[0107] L 12 represents a group represented by formula (A-4).

[0108] b and c each independently represent a number in the range of 0 to 5.)

[0109] [Chemical Formula 9]

[0110]

[0111] (In formula (A-4),

[0112] R 15 and R 16 each independently represent a divalent aromatic group optionally having a substituent,

[0113] L 13 each independently represent a single bond, or a divalent linking group optionally having a substituent, R 15 and L 13 may combine together to form a ring.)

[0114] d represents a number in the range of 0 to 5.).

[0115] The component (A) of the present invention functions as a crosslinking agent for the (B) maleimide resin. The resin composition of the present invention containing the component (A) in combination with the maleimide resin can give a cured product having excellent crack resistance. The component (A) may be used alone in one kind, or two or more kinds may be used in combination.)

[0116] In formula (A-1), X represents a divalent group represented by formula (A-2) or a divalent group represented by formula (A-3).

[0117] In formula (A-2), R 11 and R 12 each independently represent a divalent aromatic group optionally having a substituent. The divalent aromatic group means a group obtained by removing two hydrogen atoms from the aromatic ring of an aromatic compound. Examples of the divalent aromatic group optionally having a substituent include an arylene group optionally having a substituent and a heteroarylene group optionally having a substituent. The number of carbon atoms of the divalent aromatic group is preferably 3 or more, more preferably 4 or more or 5 or more, further preferably 6 or more, and the upper limit is preferably 30 or less, more preferably 24 or less, further preferably 18 or less or 14 or less, and particularly preferably 10 or less. The number of carbon atoms does not include the number of carbon atoms of the substituent.)

[0118] In a suitable embodiment, by R 11 and R 12The divalent aromatic groups represented are each independently a phenylene group optionally having a substituent; a naphthylene group optionally having a substituent; a phenylene-fluorene-phenylene group optionally having a substituent; a biphenylene group optionally having a substituent, more preferably a phenylene group optionally having a substituent or a naphthylene group optionally having a substituent, and particularly preferably a phenylene group optionally having a substituent. When the divalent aromatic group has a substituent, the substituent is the same as the substituent described above, and preferably one or more selected from alkyl, alkenyl, and hydroxyl groups, and more preferably one or more selected from methyl, allyl, and hydroxyl groups.

[0119] In formula (A-2), L 11 each independently represents a single bond or a divalent linking group optionally having a substituent. Examples of the divalent linking group optionally having a substituent include a divalent organic group formed by one or more (e.g., 1 to 3000, 1 to 1000, 1 to 100, 1 to 50) skeleton atoms selected from carbon atoms, oxygen atoms, nitrogen atoms, and sulfur atoms, and preferably an oxygen atom, a carbonyl group, a sulfonyl group, a divalent aliphatic group optionally having a substituent, or a divalent aromatic group optionally having a substituent.

[0120] In a suitable embodiment, L 11 each independently is a single bond, a divalent aliphatic group optionally having a substituent, an oxygen atom, a divalent aromatic group optionally having a substituent, a carbonyl group, or a sulfonyl group.

[0121] Examples of the divalent aliphatic group in L 11 include, for example, alkylene, cycloalkylene, alkenylene, cycloalkenylene, alkapolyene (the number of double bonds is preferably 2 to 10, more preferably 2 to 6, further preferably 2 to 4, and further more preferably 2), etc., and preferably alkylene, cycloalkylene, alkenylene, cycloalkenylene, and more preferably alkylene, cycloalkylene, and further preferably cycloalkylene.

[0122] L 11 The alkylene in may be either linear or branched, and the number of carbon atoms is preferably 1 to 12, more preferably 1 to 6, and further preferably 1 to 4. The number of carbon atoms does not include the carbon atoms of the substituent. Examples of the alkylene include methylene, ethylene, propylene, 2-propylene, 1,1-dimethyl-3-methylpropylene, butylene, pentylene, hexylene, etc.

[0123] L 11The number of carbon atoms of the subcycloalkyl group is preferably 3 to 15, more preferably 3 to 12, and still more preferably 3 to 10. This number of carbon atoms does not include the carbon atoms of the substituents. Examples of the subcycloalkyl group include, for example, cyclopropylidene, cyclobutylidene, cyclopentylidene, cyclohexylidene, decahydronaphthylidene, norbornylidene, dicyclopentylidene, adamantylidene, etc., and dicyclopentylidene is preferred.

[0124] L 11 The subalkenyl group in it can be either linear or branched, and the number of its carbon atoms is preferably 2 to 12, more preferably 2 to 6, and still more preferably 2 to 4. This number of carbon atoms does not include the carbon atoms of the substituents. Examples of the subalkenyl group include, for example, vinylidene, propenylidene, butenylidene, pentenylidene, hexenylidene, etc.

[0125] L 11 The number of carbon atoms of the subcycloalkenyl group is preferably 3 to 15, more preferably 3 to 12, and still more preferably 3 to 10. This number of carbon atoms does not include the carbon atoms of the substituents. Examples of the subcycloalkenyl group include, for example, cyclopropenylidene, cyclobutenylidene, cyclopentenylidene, cyclohexenylidene, norbornenylidene, etc.

[0126] As L 11 Examples of the divalent aromatic group in it include, for example, arylene and heteroarylene, and arylene is preferred.

[0127] L 11 The number of carbon atoms of the arylene group is preferably 6 to 24, more preferably 6 to 18, and still more preferably 6 to 14. This number of carbon atoms does not include the carbon atoms of the substituents. Examples of the arylene group include, for example, phenylene, naphthylene, anthrylene, fluorenediyl (e.g., 9H-fluorene-9,9-diyl), fluorenylene, phenanthrenediyl, indanediy, pyrenediyl, etc., and phenylene and fluorenylene are preferred.

[0128] L 11 The number of carbon atoms of the heteroarylene group is preferably 3 to 21, more preferably 3 to 15, and still more preferably 3 to 9. This number of carbon atoms does not include the carbon atoms of the substituents. Examples of the heteroarylene group include, for example, pyrrolediyl, furandiyl, thiophenediyl, pyridinediyl, pyridazinediyl, pyrimidinediyl, pyrazinediyl, triazinediyl, piperazinediyl, triazolediyl, purinediyl, carbazolediyl, quinolinediyl, isoquinolinediyl, etc.

[0129] R 11 and L 11 can combine together to form a ring. In this case, L 11 is preferably a divalent aliphatic group optionally having substituents, and more preferably an alkylene group optionally having substituents. It should be noted that when R 11 and L 11When combined to form a ring, it is preferred that a phenylene group and a cyclopentylene group are combined to form an indane ring.

[0130] L 11 Preferably, each independently represents a single bond, a divalent aliphatic group optionally having a substituent, an oxygen atom, a divalent aromatic group optionally having a substituent, a carbonyl group or a sulfonyl group. More preferably, each independently represents a single bond, a divalent aliphatic group optionally having a substituent, an oxygen atom, a phenylene group, a fluorenylene group, a carbonyl group or a sulfonyl group. Preferably, it is a single bond, an oxygen atom, a carbonyl group, a sulfonyl group, an alkylene group having 1 to 12 carbon atoms optionally having a substituent, or a cycloalkylene group having 3 to 15 carbon atoms optionally having a substituent, or an arylene group having 6 to 24 carbon atoms optionally having a substituent. L 11 The optional substituent is the substituent as described above, and preferably one or more selected from an alkyl group, an alkenyl group and a hydroxyl group, and more preferably one or more selected from a methyl group, an allyl group and a hydroxyl group.

[0131] In formula (A-2), a represents a number in the range of 0 to 5, preferably represents a number in the range of 0 to 4, more preferably represents a number in the range of 0 to 3 or 0 to 2.

[0132] In formula (A-3), R 13 and R 14 each independently represents a divalent aromatic group optionally having a substituent. The divalent aromatic group may be the same as the divalent aromatic group represented by R 11 and R 12 in formula (A-2). In a suitable embodiment, the divalent aromatic groups represented by R 13 and R 14 are each independently a phenylene group optionally having a substituent or a naphthylene group optionally having a substituent, and more preferably a phenylene group optionally having a substituent. When the divalent aromatic group has a substituent, the substituent is the substituent as described above, and preferably one or more selected from an alkyl group, an alkenyl group and a hydroxyl group, and more preferably one or more selected from a methyl group, an allyl group and a hydroxyl group.

[0133] In formula (A-3), L 12 represents the group shown in formula (A-4).

[0134] In formula (A-4), R 15 and R 16 each independently represents a divalent aromatic group optionally having a substituent. The divalent aromatic groups in R 15 and R 16 may be the same as the divalent aromatic groups represented by R 11 and R 12 in formula (A-2). In a suitable embodiment, the divalent aromatic groups represented by R 15and R 16 The divalent aromatic group represented is a phenylene group optionally having a substituent or a naphthylene group optionally having a substituent, more preferably a phenylene group optionally having a substituent. When the divalent aromatic group has a substituent, the substituent is the substituent as described above, preferably one or more selected from alkyl, alkenyl, and hydroxyl groups, more preferably one or more selected from methyl, allyl, and hydroxyl groups.

[0135] In formula (A-4), L 13 each independently represents a single bond or a divalent linking group optionally having a substituent. The divalent linking group in L 13 can be the same as the divalent linking group in formula (A-2). In a preferred embodiment, the divalent linking group represented by L 11 is an alkylene group having 1 to 12 carbon atoms optionally having a substituent. The substituent optionally possessed is the substituent as described above and can be the same as the substituent optionally possessed by L 13 . 13 In formula (A-4), d represents a number in the range of 0 to 5, preferably represents a number in the range of 0 to 4, more preferably represents a number in the range of 0 to 3, or 0 to 2. R 11 and L

[0136] can combine together to form a ring. In this case, L 15 is preferably a divalent aliphatic group optionally having a substituent, more preferably an alkylene group optionally having a substituent. It should be noted that when R 13 and L 13 combine together to form a ring, it is preferably a phenylene group combined with a cyclopentylene group to form an indane ring. 15 In formula (A-3), b and c each independently represent a number in the range of 0 to 5, preferably represent a number in the range of 0 to 4, more preferably represent a number in the range of 0 to 3, or 0 to 2. 13

[0137] Among them, from the viewpoint of a resin composition that can achieve a cured product with good dielectric properties, good mechanical properties (high elongation at break), and excellent crack resistance when combined with component (B) and component (C), when X is a divalent group represented by formula (A-2), the divalent group represented by formula (A-2), that is, X is preferably a divalent group represented by the following formula (A-5). From the same viewpoint, when X is a divalent group represented by formula (A-3), L

[0138] in formula (A-3), that is, the divalent group represented by formula (A-4) is preferably a divalent group represented by the following formula (A-5): 12

[0139] [Chemical formula 10]

[0140]

[0141] (In formula (A-5),

[0142] each Rs independently represents a substituent,

[0143] L 21 each independently represents a single bond, a divalent aliphatic group optionally having a substituent, an oxygen atom, a phenylene group, a fluorenylene group, a carbonyl group or a sulfonyl group, wherein when L 21 is a divalent aliphatic group optionally having a substituent, L 21 may combine with the benzene ring on the left to form a ring,

[0144] n1 and n2 each independently represent a number in the range of 0 to 4,

[0145] m represents a number in the range of 0 to 5,

[0146] “*” represents a connecting bond.).

[0147] Each Rs independently represents a substituent. The substituent is the substituent as described above, preferably one or more selected from alkyl, alkenyl and hydroxyl, more preferably one or more selected from methyl, allyl and hydroxyl.

[0148] L 21 each independently represents a single bond, a divalent aliphatic group optionally having a substituent, an oxygen atom, a phenylene group, a fluorenylene group, a carbonyl group or a sulfonyl group, more preferably a single bond, an oxygen atom, a carbonyl group, a sulfonyl group, an alkylene group having 1 to 12 carbon atoms optionally having a substituent, or a cycloalkylene group having 3 to 15 carbon atoms optionally having a substituent, or an arylene group having 6 to 24 carbon atoms optionally having a substituent. L 21 The substituent optionally had is the substituent as described above, preferably one or more selected from alkyl, alkenyl and hydroxyl, more preferably one or more selected from methyl, allyl and hydroxyl.

[0149] In the case where L 21 is a divalent aliphatic group optionally having a substituent, L 21 may combine with the benzene ring on the left to form a ring. In this case, it is preferred that a cyclopentylene group combines with the benzene ring on the left to form an indane ring.

[0150] n1 and n2 each independently represent a number in the range of 0 to 4, preferably represent 0 to 4, more preferably represent a number in the range of 0 to 3 or 0 to 2.

[0151] m represents a number in the range of 0 to 5, preferably represents 0 to 4, and more preferably represents a number in the ranges of 0 to 3 and 0 to 2. Among them, from the perspective of being able to more enjoy the effects of the present invention, m is preferably 1 or 2.

[0152] From the perspective of being able to more enjoy the effects of the present invention, in a particularly suitable embodiment,

[0153] X in formula (A-1) represents a divalent group shown in formula (A-2),

[0154] R 11 and R 12 each independently represents a phenylene group optionally having a substituent or a naphthylene group optionally having a substituent,

[0155] L 11 each independently represents a single bond, a divalent aliphatic group optionally having a substituent, an oxygen atom, a phenylene group, a fluorenylene group, a carbonyl group or a sulfonyl group,

[0156] a represents a number in the range of 0 to 5, R 11 and L 11 can combine together to form a ring. Among them, the divalent group shown in formula (A-2) is preferably the divalent group shown in formula (A-5). In the said embodiment, suitable types of substituents are the types as described above.

[0157] In another particularly suitable embodiment from the perspective of being able to more enjoy the effects of the present invention,

[0158] X in formula (A-1) represents a divalent group shown in formula (A-3),

[0159] R 13 and R 14 each independently represents a phenylene group optionally having a substituent,

[0160] b and c each independently represent a number in the range of 0 to 5,

[0161] L 12 is a group shown in formula (A-4),

[0162] R 15 and R 16 each independently represents a phenylene group optionally having a substituent or a naphthylene group optionally having a substituent,

[0163] L 13 each independently represents a single bond, a divalent aliphatic group optionally having a substituent, an oxygen atom, a phenylene group, a fluorenylene group, a carbonyl group or a sulfonyl group,

[0164] d represents a number in the range of 0 to 5, R 15 and L 13They can be combined to form a ring. Among them, the divalent group represented by formula (A-4) is preferably the divalent group represented by formula (A-5). In the said embodiment, the suitable types of substituents are the types as described above.

[0165] Component (A) can be obtained, for example, by causing

[0166] 1) 1-phenyl-1-propene-3-halide

[0167] 2) Divalent phenol compound

[0168] to undergo a condensation reaction.

[0169] 1-phenyl-1-propene-3-halide is a compound obtained by bonding a halogen to the 3-terminal of 1-phenyl-1-propene. Examples of such a compound include 3-bromo-1-phenyl-1-propene, etc.

[0170] The divalent phenol compound is a compound capable of reacting with the phenolic moiety of 1-phenyl-1-propene-3-halide and can form X in formula (A-1). Examples of such a compound include various bisphenol compounds such as 4,4'-methylenebis(2,6-dimethylphenol), 4,4'-(9-fluorenylidene)diphenol, 4,4'-dihydroxydiphenyl ether, 4,4'-dihydroxybenzophenone, bisphenol A, bisphenol F, 2,2'-diallylbisphenol A, bisphenol S, etc.; various biphenyl compounds such as 4,4'-dihydroxybiphenyl; dihydroxyaryl compounds such as 2,7-naphthalenediol; polyphenylene ether compounds having hydroxyl groups at both ends, etc.

[0171] In the condensation reaction, a base can also be used. Examples of the base include alkali metal hydroxides such as sodium hydroxide (caustic soda), potassium hydroxide, etc.; tertiary amines such as triethylamine, pyridine, N,N-diisopropylethylamine, etc. The base can be used alone as one kind or in combination of two or more kinds.

[0172] In addition, the condensation reaction can be carried out in a solvent-free system without using a solvent, or can also be carried out in an organic solvent system using an organic solvent. Examples of the organic solvent include ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.; acetate solvents such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, carbitol acetate, etc.; ether solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, diphenyl ether, anisole, etc.; carbitol solvents such as cellosolve, butyl carbitol, etc.; aromatic hydrocarbon solvents such as toluene, xylene, etc.; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, etc. The organic solvent can be used alone as one kind or in combination of two or more kinds.

[0173] The reaction temperature can be set, for example, in the range of 0 to 80°C. Additionally, the reaction time can be set, for example, in the range of 30 minutes to 24 hours.

[0174] After the reaction is completed, if necessary, in order to remove salts and excess starting materials as by-products from the system, purification steps such as washing with water and fine filtration can also be carried out. Specifically, after adding an amount of water required to dissolve the salts as by-products and stirring, the aqueous layer is discarded. Then, the organic layer is dried, and if necessary, the organic solvent is removed by distillation, whereby the compound of the present invention can be obtained. It can also be directly used as a solvent for the resin composition without completely removing the organic solvent.

[0175] From the viewpoint of a resin composition that can achieve a cured product as described below in combination with component (B) and component (C), when the resin component in the resin composition is set to 100% by mass, the content of component (A) is preferably 2% by mass or more, more preferably 5% by mass or more, further preferably 7% by mass or more, still further preferably 7.5% by mass or more or 8% by mass or more, and its upper limit is preferably 15% by mass or less, more preferably 12% by mass or less, further preferably 11% by mass or less, 10% by mass or less, or 9.5% by mass or less. The cured product exhibits good dielectric properties, and at the same time, by incorporating the alkylene ether skeleton of (A) into the curing system, the rigidity of maleimide is alleviated and flexibility is ensured, thus presenting good mechanical properties (high elongation at break) and excellent crack resistance. Therefore, in one embodiment, when the resin component in the resin composition is set to 100% by mass, the content of component (A) is 2% by mass or more and 12% by mass or less.

[0176] In the present invention, the so-called "resin component" of the resin composition refers to the component obtained by removing the inorganic filler described below from the non-volatile components constituting the resin composition.

[0177] In the present invention, the "non-volatile component" refers to the component other than the [solvent] described below among the components constituting the resin composition.

[0178] [(B) Maleimide resin]

[0179] The resin composition of the present invention contains a maleimide resin as component (B).

[0180] As the maleimide resin, as long as it has one or more (preferably two or more) maleimide groups (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl) in one molecule, its type is not particularly limited. Component (B) can be used alone or in combination of two or more.

[0181] (B) component may be an aromatic maleimide resin having a maleimide group directly bonded to an aromatic ring, or an aliphatic maleimide resin not having a maleimide group directly bonded to an aromatic ring. When the (B) component contains an aliphatic maleimide resin, as the aliphatic maleimide resin, a maleimide resin having a carbon skeleton derived from dimer acid is preferably included. When the (B) component contains an aromatic maleimide resin, as the aromatic maleimide resin, a maleimide resin having one or more skeletons selected from a biphenyl skeleton and an indane skeleton is preferably included. Therefore, the (B) component preferably contains a maleimide resin having one or more skeletons selected from a carbon skeleton derived from dimer acid, a biphenyl skeleton, and an indane skeleton.

[0182] The carbon skeleton derived from dimer acid refers to the carbon skeleton obtained by removing two terminal carboxyl groups (-COOH) of dimer acid, or the carbon skeleton obtained by replacing two terminal carboxyl groups (-COOH) with methylene groups (-CH 2 -). Dimer acid is a known compound obtained by dimerizing an unsaturated fatty acid (preferably an unsaturated fatty acid having 11 to 22 carbon atoms, more preferably an unsaturated fatty acid having 14 to 20 carbon atoms, and particularly preferably an unsaturated fatty acid having 18 carbon atoms), and its industrial manufacturing process is generally standardized in the industry. For dimer acid, in particular, a substance mainly composed of dimer acid having 36 carbon atoms obtained by dimerizing inexpensive and easily available unsaturated fatty acids having 18 carbon atoms such as oleic acid and linoleic acid can be easily obtained. In addition, dimer acid may contain any amount of monomer acid, trimer acid, other polymerized fatty acids, etc. depending on the manufacturing method, purification degree, etc. In addition, although double bonds remain after the polymerization reaction of the unsaturated fatty acid, in this specification, a hydrogenated product obtained by further performing a hydrogenation reaction to reduce the degree of unsaturation is also included in dimer acid.

[0183] The maleimide resin having a carbon skeleton derived from dimer acid preferably contains a maleimide resin represented by the following formula (B1):

[0184] [Chemical formula 11]

[0185]

[0186] (In formula (B1),

[0187] n 1 +1 X's each independently represent a divalent organic group formed by 5 or more skeleton atoms selected from carbon atoms, nitrogen atoms (not forming an imide), oxygen atoms, and sulfur atoms and non-skeleton atoms selected from hydrogen atoms and halogen atoms, and at least 1 of the n + 1 X's represents a divalent hydrocarbon group derived from dimer acid;

[0188] n1 Each Y independently represents a tetravalent organic group formed from 5 or more skeletal atoms selected from carbon atoms, nitrogen atoms (not forming imides), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms;

[0189] n 1 represents an integer of 0 or more.

[0190] In formula (B1), n 1 Each of n + 1 Xs independently represents a divalent organic group formed from 5 or more (preferably 5 to 200, more preferably 5 to 100, still more preferably 5 to 50) skeletal atoms selected from carbon atoms, nitrogen atoms (not forming imides), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms, and at least one of the n + 1 Xs represents a divalent hydrocarbon group derived from a dimer acid.

[0191] The divalent hydrocarbon group derived from a dimer acid means a divalent hydrocarbon group obtained by removing the two terminal carboxyl groups (-COOH) of the dimer acid, or a divalent hydrocarbon group in which the two terminal carboxyl groups (-COOH) are replaced by methylene groups (-CH 2 -).

[0192] n 1 Each of n + 1 Xs optionally has a divalent organic group other than the divalent hydrocarbon group derived from a dimer acid. When the total of n + 1 Xs is set to 100 mol%, preferably 30 mol% or more thereof is the divalent hydrocarbon group derived from a dimer acid, more preferably 60 mol% or more, still more preferably 90 mol% or more, and even more preferably all of the n 1 + 1 Xs are the divalent hydrocarbon group derived from a dimer acid. 1 + 1 Xs (all) are the divalent hydrocarbon group derived from a dimer acid.

[0193] n 1 The divalent organic group other than the divalent hydrocarbon group derived from a dimer acid among the n + 1 Xs may be a divalent organic group without an aromatic ring or a divalent organic group with an aromatic ring.

[0194] In formula (B1), n 1 Each of n Ys independently represents a tetravalent organic group formed from 5 or more (preferably 5 to 200, more preferably 5 to 100, still more preferably 5 to 50) skeletal atoms selected from carbon atoms, nitrogen atoms (not forming imides), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms. The tetravalent organic group represented by Y may be a tetravalent organic group without an aromatic ring or a tetravalent organic group with an aromatic ring.

[0195] The tetravalent organic group represented by Y is preferably a tetravalent group selected from the following formulas (Y1) to (Y5) in one embodiment:

[0196] [Chemical formula 12]

[0197]

[0198] (In the formulas (Y1) to (Y5),

[0199] Ring Y 11 、Ring Y 21 、Ring Y 22 、Ring Y 31 、Ring Y 32 、Ring Y 33 、Ring Y 41 、Ring Y 42 、Ring Y 43 、Ring Y 44 、Ring Y 51 、Ring Y 52 、Ring Y 53 、Ring Y 54 and Ring Y 55 each independently represent an optionally substituted aromatic ring or an optionally substituted non-aromatic ring;

[0200] Y 2a 、Y 3a 、Y 3b 、Y 4a 、Y 4b 、Y 4c 、Y 5a 、Y 5b 、Y 5c and Y 5d each independently represent a single bond, -C(R y ) 2 -, -O-, -CO-, -S-, -SO-, -SO 2 -, -CONH- or -NHCO-;

[0201] R y each independently represents a hydrogen atom or an alkyl group optionally substituted by a halogen atom, or two R y bonded to the same carbon atom are combined together to form an optionally substituted non-aromatic ring;

[0202] * represents a bonding site;

[0203] (The two bonding sites on the same ring represented by * are the bonding sites of two adjacent carbon atoms on the ring.).

[0204] In the formulas (Y1) to (Y5), Ring Y 11 、Ring Y 21, Ring Y 22 , Ring Y 31 , Ring Y 32 , Ring Y 33 , Ring Y 41 , Ring Y 42 , Ring Y 43 , Ring Y 44 , Ring Y 51 , Ring Y 52 , Ring Y 53 , Ring Y 54 and Ring Y 55 Each independently represents an optionally substituted aromatic ring or an optionally substituted non-aromatic ring. These ring structures are preferably optionally substituted aromatic rings, more preferably optionally substituted benzene rings, and further preferably benzene rings optionally substituted with alkyl groups.

[0205] As Ring Y 11 , Ring Y 21 , Ring Y 22 , Ring Y 31 , Ring Y 32 , Ring Y 33 , Ring Y 41 , Ring Y 42 , Ring Y 43 , Ring Y 44 , Ring Y 51 , Ring Y 52 , Ring Y 53 , Ring Y 54 and Ring Y 55 The substituents that Ring Y can have are not particularly limited, and examples thereof include halogen atoms, -NO 2 , -CN, -COH, -OH, -SH, -NH 2 , -COOH, -R c , -COR c , -OR c , -SR c , -SOR c , -SO 2 R c , -NHR c , -NR c 2 , -COOR c , -OCOR c , -CONH 2 , -CONHR c , -CONR c 2 , -NHCOR c and other monovalent substituents (wherein, R c is as shown in the above substituents.).

[0206] In formulas (Y1) to (Y5), Y 2a 、Y 3a 、Y 3b 、Y 4a 、Y 4b 、Y 4c 、Y 5a 、Y 5b 、Y 5c and Y 5d each independently represents a single bond, -C(R y ) 2 -, -O-, -CO-, -S-, -SO-, -SO 2 -, -CONH- or -NHCO-, and in one embodiment is preferably a single bond, -C(R y ) 2 - or -O-.

[0207] R y each independently represents a hydrogen atom or an alkyl group optionally substituted by a halogen atom, or two R y bonded to the same carbon atom are combined together to form a non-aromatic ring optionally having a substituent. The alkyl group may also be the same as the alkyl group in R c . R y each independently preferably represents a hydrogen atom or an alkyl group optionally substituted by a halogen atom; more preferably represents a hydrogen atom or a methyl group optionally substituted by a halogen atom; still more preferably represents a hydrogen atom, a methyl group or a trifluoromethyl group; particularly preferably represents a hydrogen atom or a methyl group.

[0208] As substituents that R y may have, there is no particular limitation, and examples thereof include a halogen atom, -NO 2 , -CN, -COH, -OH, -SH, -NH 2 , -COOH, -R c , -COR c , -OR c , -SR c , -SOR c , -SO 2 R c , -NHR c , -NR c 2 , -COOR c , -OCOR c , -CONH 2 , -CONHR c , -CONR c 2 , -NHCOR c and other monovalent substituents (wherein, R c is as described above).

[0209] In formula (B1), n 1 represents an integer of 0 or more, preferably an integer of 0 or 1 to 10, more preferably 0.

[0210] The maleimide resin having a carbon skeleton derived from dimer acid can be used alone or in combination of two or more.

[0211] Examples of commercially available maleimide resins having a carbon skeleton derived from dimer acid include "BMI-689", "BMI-1500", "BMI-1700", "BMI-3000J" manufactured by DesignerMolecules, and "SLK-6895-T90" manufactured by Shin-Etsu Chemical Co., Ltd.

[0212] Examples of the aromatic maleimide resin include the maleimide resin represented by formula (B2):

[0213] [Chemical formula 13]

[0214]

[0215] (In formula (B2),

[0216] R 10 each independently represents a hydrogen atom or an alkyl group optionally substituted by a halogen atom;

[0217] Ring D each independently represents an aromatic carbocyclic ring optionally having a substituent;

[0218] n 2 represents an integer of 1 or more;

[0219] n 2 The n units may be the same for each unit or different. ).

[0220] In formula (B2), R 10 each independently represents a hydrogen atom or an alkyl group optionally substituted by a halogen atom. The alkyl group may also be the same as the alkyl group in R c . R 10 each independently preferably represents a hydrogen atom or an alkyl group; more preferably represents a hydrogen atom or a methyl group; still more preferably represents a hydrogen atom.

[0221] In formula (B2), ring D each independently represents an aromatic carbocyclic ring optionally having a substituent. The aromatic carbocyclic ring may also be the same as ring Y 11 , ring Y 21 , ring Y 22 , ring Y 31 , ring Y 32 , ring Y 33 , ring Y 41, Ring Y 42 , Ring Y 43 , Ring Y 44 , Ring Y 51 , Ring Y 52 , Ring Y 53 , Ring Y 54 and Ring Y 55 are the same as the aromatic carbocyclic rings described in the aromatic ring terms of Ring Y. Additionally, the "substituents" in Ring D can, for example, also be the same as those in the "optionally substituted aromatic ring" of Ring Y 11 , Ring Y 21 , Ring Y 22 , Ring Y 31 , Ring Y 32 , Ring Y 33 , Ring Y 41 , Ring Y 42 , Ring Y 43 , Ring Y 44 , Ring Y 51 , Ring Y 52 , Ring Y 53 , Ring Y 54 and Ring Y 55 . Ring D preferably represents an optionally substituted benzene ring; more preferably represents a benzene ring optionally substituted with a group selected from alkyl and aryl; particularly preferably represents an (unsubstituted) benzene ring.

[0222] In formula (B2), n 2 represents an integer of 1 or more, preferably an integer of 1 to 10.

[0223] The maleimide resin having a biphenyl skeleton preferably contains a maleimide resin represented by the following formula (B3):

[0224] [Chemical formula 14]

[0225]

[0226] (In formula (B3),

[0227] R 20 each independently represents a hydrogen atom, or an alkyl group optionally substituted with a halogen atom;

[0228] Ring E, Ring F, and Ring G each independently represent an optionally substituted aromatic carbocyclic ring;

[0229] n 3 represents an integer of 1 or more;

[0230] n 3 The n units can be the same for each unit or different.).

[0231] In formula (B3), R 20Each independently represents a hydrogen atom or an alkyl group optionally substituted with a halogen atom. The alkyl group may also be the same as the alkyl group in R c . R 20 Each independently is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and still more preferably a hydrogen atom.

[0232] In formula (B3), ring E, ring F, and ring G each independently represent an aromatic carbocyclic ring optionally having substituents. The aromatic carbocyclic ring may also be the same as the aromatic carbocyclic ring described in the aromatic ring terms of ring Y 11 , ring Y 21 , ring Y 22 , ring Y 31 , ring Y 32 , ring Y 33 , ring Y 41 , ring Y 42 , ring Y 43 , ring Y 44 , ring Y 51 , ring Y 52 , ring Y 53 , ring Y 54 and ring Y 55 . Ring E, ring F, and ring G are preferably benzene rings optionally having substituents, more preferably benzene rings optionally substituted with a group selected from an alkyl group and an aryl group, and still more preferably (unsubstituted) benzene rings.

[0233] As the substituents that ring E, ring F, and ring G may have, there is no particular limitation, and examples thereof include a halogen atom, -NO 2 , -CN, -COH, -OH, -SH, -NH 2 , -COOH, -R c , -COR c , -OR c , -SR c , -SOR c , -SO 2 R c , -NHR c , -NR c 2 , -COOR c , -OCOR c , -CONH 2 , -CONHR c , -CONR c 2 , -NHCOR c and other monovalent substituents (wherein R c is as described above).

[0234] In formula (B3), n 3represents an integer of 1 or more, preferably an integer of 1 to 10.

[0235] As commercially available products of maleimide resins having a biphenyl skeleton, for example, "MIR-3000-70MT", "MIR-5000-60T", etc. manufactured by Nippon Kayaku Co., Ltd. can be cited.

[0236] The maleimide resin having a biphenyl skeleton can be used alone as one kind, or two or more kinds can be used in combination.

[0237] The maleimide resin having an indane skeleton preferably contains the maleimide resin represented by the following formula (B4):

[0238] [Chemical formula 15]

[0239]

[0240] (In formula (B4),

[0241] R 30 each independently represents an alkyl group;

[0242] Ring H and Ring I each independently represent an optionally substituted aromatic carbocyclic ring;

[0243] n 4 represents an integer of 1 or more;

[0244] n 4 The units may be the same or different for each unit.).

[0245] In formula (B4), R 30 each independently represents an alkyl group. R 30 is preferably methyl.

[0246] In formula (B4), Ring H each independently represents an optionally substituted aromatic ring. Ring H is preferably an optionally substituted benzene ring, more preferably an optionally alkyl-substituted benzene ring, and further preferably an alkyl-substituted benzene ring.

[0247] In formula (B4), Ring I each independently represents an optionally substituted aromatic ring. Ring I is preferably an optionally substituted benzene ring, more preferably an optionally alkyl-substituted benzene ring, and further preferably an (unsubstituted) benzene ring.

[0248] Examples of the substituents that Ring H and Ring I may have are not particularly limited, and include, for example, a halogen atom, -NO 2 , -CN, -COH, -OH, -SH, -NH 2 , -COOH, -R c , -COR c , -ORc 、 -SR c 、 -SOR c 、 -SO 2 R c 、 -NHR c 、 -NR c 2 、 -COOR c 、 -OCOR c 、 -CONH 2 、 -CONHR c 、 -CONR c 2 、 -NHCOR c and monovalent substituents such as -NHCOR (where R c is as described above).

[0249] In formula (B4), n 4 represents an integer of 1 or more, preferably an integer of 1 to 20.

[0250] The maleimide resin having an indane skeleton can be produced, for example, by the method described in Japanese Invention Association Publication Bulletin No. 2020 - 500211 or a method based thereon.

[0251] The maleimide resin having an indane skeleton can be used alone or in combination of two or more kinds.

[0252] The maleimide group equivalent of component (B) is preferably 50 g / eq. or more, more preferably 100 g / eq. or more, still more preferably 150 g / eq. or more, 200 g / eq. or more, 250 g / eq. or more, or 300 g / eq. or more, and the upper limit is preferably 2000 g / eq. or less, more preferably 1000 g / eq. or less, still more preferably 800 g / eq. or less, 600 g / eq. or less, 500 g / eq. or less, or 450 g / eq. or less. The maleimide group equivalent is the mass of component (B) per 1 molar equivalent of the maleimide group.

[0253] The molecular weight of component (B) is preferably less than 5000, more preferably less than 3000, still more preferably less than 2000, less than 1500, less than 1200, or less than 1000, and the lower limit is not particularly limited and can be, for example, 300 or more, 400 or more, 500 or more, etc.

[0254] From the viewpoint of a resin composition capable of achieving a cured product that exhibits good dielectric properties, good mechanical properties (high elongation at break), and excellent crack resistance when combined with component (A) and component (C), when the resin component in the resin composition is set to 100% by mass, the content of component (B) is preferably 20% by mass or 30% by mass or more, more preferably 40% by mass or more, still more preferably 45% by mass or more or 50% by mass or more, and the upper limit of its content is preferably 80% by mass or less, more preferably 75% by mass or less, still more preferably 70% by mass or less or 65% by mass or less. Therefore, in one embodiment, when the resin component in the resin composition is set to 100% by mass, the content of component (B) is 20% by mass or more and 75% by mass or less.

[0255] From the viewpoint of a resin composition capable of achieving a cured product that exhibits even better dielectric properties, better mechanical properties (high elongation at break), and more excellent crack resistance when combined with component (C), the mass ratio of component (A) to component (B) ((A) component / (B) component) is preferably 0.02 or more, more preferably 0.04, still more preferably 0.06 or more or 0.08 or more, even more preferably 0.1 or more, 0.12 or more or 0.14 or more, and the upper limit is preferably 0.4 or less, more preferably 0.3 or less, still more preferably 0.25 or less or 0.2 or less.

[0256] [(C) thermosetting resin]

[0257] The resin composition of the present invention contains a thermosetting resin as component (C). The thermosetting resin as component (C) does not contain a maleimide resin.

[0258] Examples of component (C) include, for example, epoxy resins, phenolic resins, benzoxazine resins, reactive ester resins, cyanate ester resins, carbodiimide resins, amine resins, acid anhydride resins, terminal double bond resins, etc. The thermosetting resin can be used alone or in combination of two or more in any ratio. Among them, from the viewpoint of more enjoying the effects of the present invention, it is preferably one or more selected from epoxy resins, phenolic resins, and terminal double bond resins.

[0259] It should be noted that phenolic resins, naphthol resins, benzoxazine resins, reactive ester resins, cyanate ester resins, carbodiimide resins, amine resins, and acid anhydride resins also have the function of curing agents for epoxy resins, and they are also collectively referred to as epoxy resin curing agents.

[0260] - Epoxy resin -

[0261] The type of the epoxy resin is not particularly limited as long as it has one or more (preferably two or more) epoxy groups in one molecule. Examples of the epoxy resin include bisphenol type epoxy resins, dicyclopentadiene type epoxy resins, triphenol type epoxy resins, naphthol novolak type epoxy resins, phenol novolak type epoxy resins, tert-butyl-catechol type epoxy resins, naphthalene type epoxy resins, naphthol type epoxy resins, anthracene type epoxy resins, glycidylamine type epoxy resins, glycidyl ester type epoxy resins, cresol novolak type epoxy resins, biphenyl type epoxy resins, linear aliphatic epoxy resins, epoxy resins having a butadiene structure, alicyclic epoxy resins, heterocyclic epoxy resins, epoxy resins containing a spiro ring, cyclohexane type epoxy resins, cyclohexanedimethanol type epoxy resins, naphthyl ether type epoxy resins, trimethylol type epoxy resins, and tetraphenylethane type epoxy resins. The bisphenol type epoxy resin refers to an epoxy resin having a bisphenol structure, and examples thereof include bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, and bisphenol AF type epoxy resins. The biphenyl type epoxy resin refers to an epoxy resin having a biphenyl structure, and here, the biphenyl structure may optionally have substituents such as an alkyl group, an alkoxy group, and an aryl group. Therefore, xylenol type epoxy resins and biphenyl aralkyl type epoxy resins are also included in the biphenyl type epoxy resins.

[0262] Epoxy resins can be classified into epoxy resins that are liquid at a temperature of 20°C (hereinafter referred to as "liquid epoxy resins") and epoxy resins that are solid at a temperature of 20°C (hereinafter referred to as "solid epoxy resins"). As the component (C), the resin composition of the present invention may contain only a liquid epoxy resin, only a solid epoxy resin, or a combination of a liquid epoxy resin and a solid epoxy resin.

[0263] As the liquid epoxy resin, a liquid epoxy resin having two or more epoxy groups in one molecule is preferred.

[0264] As the liquid epoxy resin, GLYCIROL type epoxy resins, bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol AF type epoxy resins, naphthalene type epoxy resins, glycidyl ester type epoxy resins, glycidylamine type epoxy resins, phenol novolak type epoxy resins, alicyclic epoxy resins having an ester skeleton, cyclohexanedimethanol type epoxy resins, cyclic aliphatic glycidyl ethers, and epoxy resins having a butadiene structure are preferred.

[0265] As specific examples of the liquid epoxy resin, there can be mentioned "EX-992L" manufactured by Nagase ChemteX Corporation, "YX7400" manufactured by Mitsubishi Chemical Corporation, "HP4032", "HP4032D", "HP4032SS" (naphthalene-type epoxy resin) manufactured by DIC Corporation; "828US", "828EL", "825" (bisphenol A-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER807", "1750" (bisphenol F-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER152" (phenol novolac-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "630", "630LSD", "604" (glycidylamine-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "ED-523T" (GLYCIROL-type epoxy resin) manufactured by ADEKA Corporation; "EP-3950L", "EP-3980S" (glycidylamine-type epoxy resin) manufactured by ADEKA Corporation; "EP-4088S" (dicyclopentadiene-type epoxy resin) manufactured by ADEKA Corporation; "ZX1059" (a mixture of bisphenol A-type epoxy resin and bisphenol F-type epoxy resin) manufactured by Nippon Steel Chemical Co., Ltd.; "EX-721" (glycidyl ester-type epoxy resin) manufactured by Nagase ChemteX Corporation; "EX-991L" (epoxy resin containing an alkyleneoxy skeleton) manufactured by Nagase ChemteX Corporation; "Celloxide 2021P" (alicyclic epoxy resin having an ester skeleton) manufactured by Daicel Corporation; "PB-3600" manufactured by Daicel Corporation, "JP-100", "JP-200" (epoxy resin having a butadiene structure) manufactured by Nippon Soda Co., Ltd.; "ZX1658", "ZX1658GS" (liquid 1,4-glycidylcyclohexane-type epoxy resin) manufactured by Osaka Gas Chemical Co., Ltd.; "EG-280" (epoxy resin containing a fluorene structure) manufactured by Osaka Gas Chemical Co., Ltd.; "EX-201" (resorcinol-type epoxy resin) manufactured by Nagase ChemteX Corporation, etc.

[0266] As the solid epoxy resin, a solid epoxy resin having 3 or more epoxy groups in 1 molecule is preferred, and an aromatic solid epoxy resin having 3 or more epoxy groups in 1 molecule is more preferred.

[0267] As the solid epoxy resin, preferably bixylenol type epoxy resin, naphthalene type epoxy resin, naphthalene type tetrafunctional epoxy resin, naphthol novolac type epoxy resin, cresol novolac type epoxy resin, dicyclopentadiene type epoxy resin, triphenol type epoxy resin, naphthol type epoxy resin, biphenyl type epoxy resin, naphthylidene ether type epoxy resin, anthracene type epoxy resin, bisphenol A type epoxy resin, bisphenol AF type epoxy resin, phenol aralkyl type epoxy resin, tetraphenylethane type epoxy resin, phenol phthalimidine type epoxy resin.

[0268] As specific examples of solid epoxy resins, there can be mentioned "HP4032H" (naphthalene-type epoxy resin) manufactured by DIC Corporation; "HP-4700", "HP-4710" (naphthalene-type tetrafunctional epoxy resins) manufactured by DIC Corporation; "N-690" (cresol novolak-type epoxy resin) manufactured by DIC Corporation; "N-695" (cresol novolak-type epoxy resin) manufactured by DIC Corporation; "HP-7200", "HP-7200HH", "HP-7200H", "HP-7200L" (dicyclopentadiene-type epoxy resins) manufactured by DIC Corporation; "EXA-7311", "EXA-7311-G3", "EXA-7311-G4", "EXA-7311-G4S", "HP-6000", "HP-6000L" (naphthyl ether-type epoxy resins) manufactured by DIC Corporation; "EPPN-502H" (triphenol-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC7000L" (naphthol novolak-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC3000H", "NC3000", "NC3000L", "NC3000FH", "NC3100" (biphenyl-type epoxy resins) manufactured by Nippon Kayaku Co., Ltd.; "ESN475V", "ESN4100V" (naphthalene-type epoxy resins) manufactured by Nippon Steel Chemical Co., Ltd.; "ESN485" (naphthol-type epoxy resin) manufactured by Nippon Steel Chemical Co., Ltd.; "ESN375" (dihydroxynaphthalene-type epoxy resin) manufactured by Nippon Steel Chemical Co., Ltd.; "YX4000H", "YX4000", "YX4000HK", "YL7890" (xylenol-type epoxy resins) manufactured by Mitsubishi Chemical Corporation; "YL6121" (biphenyl-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX8800" (anthracene-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX7700" (phenol aralkyl-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "PG-100", "CG-500" manufactured by Osaka Gas Chemical Co., Ltd.; "YL7760" (bisphenol AF-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YL7800" (fluorene-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1010" (bisphenol A-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1031S" (tetraphenylethane-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "WHR991S" (phenol benzopyrrolidone-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd., etc. They can be used alone, or two or more of them can be used in combination.

[0269] When using a combination of a liquid epoxy resin and a solid epoxy resin as the epoxy resin, their mass ratio (liquid epoxy resin: solid epoxy resin) is preferably 10:1 to 1:50, more preferably 5:1 to 1:20, still more preferably 2:1 to 1:10, and particularly preferably 1:1 to 1:3.

[0270] The epoxy equivalent of the epoxy resin is preferably 50 g / eq. to 5000 g / eq., more preferably 60 g / eq. to 2000 g / eq., further preferably 70 g / eq. to 1000 g / eq., and even further preferably 80 g / eq. to 500 g / eq. The epoxy equivalent is the mass of the resin per 1 equivalent of epoxy groups. This epoxy equivalent can be measured according to JIS K 7236.

[0271] The weight-average molecular weight of the epoxy resin is preferably 100 to 5000, more preferably 250 to 3000, and further preferably 400 to 1500. The weight-average molecular weight of the resin can be measured by gel permeation chromatography (GPC) as a value converted to polystyrene.

[0272] -Phenolic resin-

[0273] As the phenolic resin, a compound having one or more, preferably two or more hydroxyl groups bonded to an aromatic ring such as a benzene ring or a naphthalene ring in one molecule can be used. When the phenolic resin is combined with the epoxy resin, it can react with the epoxy resin to cure the resin composition, and thus is sometimes called a "phenolic curing agent". From the viewpoint of significantly obtaining the effects of the present invention, the phenolic resin is preferably a phenolic resin having a novolak structure. In addition, from the viewpoint of adhesion, a nitrogen-containing phenolic resin is preferred, and a phenolic resin containing a triazine skeleton is more preferred. Among them, from the viewpoint of significantly obtaining the effects of the present invention, a phenol novolak resin containing a triazine skeleton is preferred. Specific examples of the phenolic resin include, for example, "MEH-7700", "MEH-7810", "MEH-7851" manufactured by Meiko Kasei Co., Ltd., "NHN", "CBN", "GPH" manufactured by Nippon Kayaku Co., Ltd., "SN-170", "SN-180", "SN-190", "SN-475", "SN-485", "SN-495", "SN-375", "SN-395" manufactured by Nippon Steel Chemical & Material Co., Ltd., "LA-7052", "LA-7054", "LA-3018", "LA-3018-50P", "LA-1356", "TD2090", "TD-2090-60M", "KA-1163" manufactured by DIC Corporation, etc.

[0274] -Cyanate ester resin-

[0275] As the cyanate ester resin, a compound having one or more, preferably two or more cyanate ester groups in one molecule can be used. When combined with an epoxy resin, the cyanate ester resin can react with the epoxy resin to cure the resin composition, and thus is sometimes referred to as a "cyanate ester-based curing agent". Examples of the cyanate ester resin include: bisphenol A dicyanate, polyphenol cyanate (oligo(3-methylenephenylene cyanate)), 4,4'-methylenebis(2,6-dimethylphenyl cyanate), 4,4'-ethylenediphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanatephenyl)propane, 1,1-bis(4-cyanatephenyl)methane, bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanatephenyl-1-(methylethylene))benzene, bis(4-cyanatephenyl) sulfide, and bis(4-cyanatephenyl) ether, etc., difunctional cyanate ester resins; polyfunctional cyanate ester resins derived from phenol novolak resins, cresol novolak resins, etc.; prepolymers obtained by triazine formation of a part of these cyanate ester resins, etc. Specific examples of the cyanate ester resin include "PT30" and "PT60" (both are phenol novolak type polyfunctional cyanate ester resins), "BA230", "BA230S75" (prepolymers in which a part or all of bisphenol A dicyanate is triazine-formed to form a trimer), etc. manufactured by arxada company.

[0276] -Reactive ester resin-

[0277] As the active ester resin, it is generally preferable to use compounds having two or more highly reactive ester groups in one molecule, such as phenol esters, benzenethiol esters, N-hydroxyamine esters, esters of heterocyclic hydroxy compounds, etc. When combined with an epoxy resin, the active ester resin can react with the epoxy resin to cure the resin composition, and thus is sometimes referred to as an "active ester-based curing agent". The active ester resin is preferably a compound obtained by a condensation reaction of a carboxylic acid compound and / or a thiocarboxylic acid compound with a hydroxy compound and / or a thiol compound. In particular, from the viewpoint of improving heat resistance, an active ester resin obtained from a carboxylic acid compound and a hydroxy compound is preferred, and an active ester resin obtained from a carboxylic acid compound and a phenol compound and / or a naphthol compound is more preferred. As the carboxylic acid compound, any of aromatic carboxylic acid compounds and aliphatic carboxylic acid compounds can be used, and examples thereof include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid, and their halides. As the aromatic hydroxy compound, examples include (i) a polyaddition product of an unsaturated aliphatic cyclic compound having two double bonds in one molecule and a phenol; (ii) various bisphenol compounds; (iii) an aromatic polyol having two or more hydroxy groups bonded to carbon atoms on the aromatic ring; (iv) an aromatic monohydric alcohol having one hydroxy group bonded to a carbon atom on the aromatic ring. As the polyaddition product of an unsaturated aliphatic cyclic compound and a phenol, examples include polyaddition products of unsaturated aliphatic cyclic compounds such as dicyclopentadiene, tetrahydroindene, norbornadiene, limonene, vinylcyclohexene and phenols optionally having substituents (such as phenol, cresol, xylenol, ethylphenol, propylphenol, vinylphenol, allylphenol, phenylphenol, benzylphenol, halogenated phenol, etc.), and specifically, examples include dicyclopentadiene-phenol type polymers. As the bisphenol compound, examples include bisphenol A, bisphenol F, bisphenol AF, bisphenol AP, bisphenol B, bisphenol BP, bisphenol C, bisphenol M. As the aromatic polyol having two or more hydroxy groups bonded to carbon atoms on the aromatic ring, examples include hydroquinone, resorcinol, catechol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, pyrogallol, phenol novolak resin. As the aromatic monohydric alcohol having one hydroxy group bonded to a carbon atom on the aromatic ring, examples include phenol, cresol, xylenol, ethylphenol, propylphenol, vinylphenol, allylphenol, phenylphenol, benzylphenol, halogenated phenol, naphthol, methylnaphthol, dimethylnaphthol, ethylnaphthol, propylnaphthol, vinylnaphthol, allylnaphthol, phenylnaphthol, benzylnaphthol, halogenated naphthol.

[0278] Specifically, as the active ester resin, a dicyclopentadiene type active ester resin, a naphthalene type active ester resin containing a naphthalene structure, an active ester resin containing an acetylated product of novolak phenol, an active ester resin containing a benzoylated product of novolak phenol, and an active ester resin containing a styryl group and a naphthalene structure are preferred, and at least one selected from a dicyclopentadiene type active ester resin and a naphthalene type active ester resin is more preferred. As the dicyclopentadiene type active ester resin, an active ester resin containing a dicyclopentadiene type diphenol structure is preferred.

[0279] Examples of commercially available products of the active ester resin include, for example, active ester resins containing a dicyclopentadiene type diphenol structure such as "EXB9451", "EXB9460", "EXB9460S", "EXB-8000L", "EXB-8000L-65M", "EXB-8000L-65TM", "HPC-8000L-65TM", "HPC-8000L-65T", "HPC-8000", "HPC-8000-65T", "EXB-8000H" (manufactured by DIC Corporation); active ester resins containing a naphthalene structure such as "EXB-8100L-65T", "EXB-8150-60T", "EXB-8150-62T", "EXB-9416-70BK", "HPC-8150-62T", "EXB-8" (manufactured by DIC Corporation); phosphorus-containing active ester resins such as "EXB9401" (manufactured by DIC Corporation); active ester resins containing an acetylated product of novolak phenol such as "DC808" (manufactured by Mitsubishi Chemical Corporation); active ester resins containing a benzoylated product of novolak phenol such as "YLH1026", "YLH1030", "YLH1048" (manufactured by Mitsubishi Chemical Corporation); active ester resins containing a styryl group and a naphthalene structure such as "PC1300-02-65MA" (manufactured by AIR&WATER Corporation), etc.

[0280] -Carbodiimide resin-

[0281] As the carbodiimide resin, a compound having one or more, preferably two or more carbodiimide structures in one molecule can be used. When combined with an epoxy resin, the carbodiimide resin can react with the epoxy resin to cure the resin composition, and thus is sometimes referred to as a "carbodiimide-based curing agent". Specific examples of the carbodiimide resin include aliphatic biscarbodiimides such as tetramethylene-bis(tert-butylcarbodiimide) and cyclohexane bis(methylene-tert-butylcarbodiimide); biscarbodiimides such as phenyl-bis(xylenylcarbodiimide); aliphatic polycarbodiimides such as polyhexamethylene carbodiimide, polytrimethylhexamethylene carbodiimide, polycyclohexylene carbodiimide, poly(methylenebiscyclohexylene carbodiimide), and poly(isophorone carbodiimide); and aromatic polycarbodiimides such as poly(phenylcarbodiimide), poly(naphthylcarbodiimide), poly(tolylene carbodiimide), poly(methyldiisopropylphenylcarbodiimide), poly(triethylphenylcarbodiimide), poly(diethylphenylcarbodiimide), poly(triisopropylphenylcarbodiimide), poly(diisopropylphenylcarbodiimide), poly(xylenylcarbodiimide), poly(tetramethylxylenylcarbodiimide), poly(methylenediphenylcarbodiimide), and poly[methylenebis(methylphenyl)carbodiimide]. Commercially available products of the carbodiimide resin include, for example, "CARBODILITE V-02B", "CARBODILITE V-03", "CARBODILITE V-04K", "CARBODILITE V-07", and "CARBODILITE V-09" manufactured by Nisshinbo Chemical Inc.; "Stabaxol P", "Stabaxol P400", "Hycasyl 510", etc. manufactured by LANXESS Corporation.

[0282] -Anhydride resin-

[0283] As the acid anhydride resin, a compound having one or more, preferably two or more acid anhydride groups in one molecule can be used. When combined with an epoxy group, the acid anhydride resin can react with the epoxy resin to cure the resin composition, and thus is sometimes referred to as an "acid anhydride-based curing agent". Specific examples of the acid anhydride resin include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, hydrogenated methylnadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenyl succinic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenone tetracarboxylic dianhydride, biphenyltetracarboxylic dianhydride, naphthalenetetracarboxylic dianhydride, oxydiphthalic dianhydride, 3,3',4,4'-diphenylsulfone tetracarboxylic dianhydride, 1,3,3a,4,5,9b-hexahydro-5-(tetrahydro-2,5-dioxo-3-furanyl)-naphtho[1,2-c]furan-1,3-dione, ethylene glycol bis(trimellitic anhydride ester), polymer-type acid anhydrides such as styrene-maleic acid resin obtained by copolymerizing styrene and maleic acid, etc. Commercially available products of the acid anhydride resin include, for example, "HNA-100", "MH-700", "MTA-15", "DDSA", "OSA" manufactured by Shin Nippon Rika Co., Ltd.; "YH-306", "YH-307" manufactured by Mitsubishi Chemical Corporation; "HN-2200", "HN-5500" manufactured by Resonac; "EF-30", "EF-40", "EF-60", "EF-80" manufactured by Cray Valley Company, etc.

[0284] -amine resin-

[0285] As the amine resin, a compound having one or more, preferably two or more amino groups in one molecule can be used. When combined with an epoxy group, the amine resin can react with the epoxy resin to cure the resin composition, and thus is sometimes referred to as an "amine-based curing agent". As the amine resin, for example, aliphatic amines, polyether amines, alicyclic amines, aromatic amines, etc. can be cited. Among them, aromatic amines are preferred. The amine resin is preferably a primary amine or a secondary amine, and more preferably a primary amine. Specific examples of the amine resin include 4,4'-methylenebis(2,6-dimethylaniline), 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, m-phenylenediamine, m-xylylenediamine, diethyltoluenediamine, 4,4'-diaminodiphenyl ether, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, 2,2-bis(3-amino-4-hydroxyphenyl)propane, 3,3-dimethyl-5,5-diethyl-4,4-diphenylmethanediamine, 2,2-bis(4-aminophenyl)propane, 2,2-bis(4-(4-aminophenoxy)phenyl)propane, 1,3-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, 4,4'-bis(4-aminophenoxy)biphenyl, bis(4-(4-aminophenoxy)phenyl)sulfone, bis(4-(3-aminophenoxy)phenyl)sulfone, etc. Commercially available products of the amine resin include, for example, "SEIKACURE-S" manufactured by SEIKA Corporation; "KAYABOND C-200S", "KAYABOND C-100", "KAYAHARDA-A", "KAYAHARDA-B", "KAYAHARDA-S" manufactured by Nippon Kayaku Co., Ltd.; "EPICURE W" manufactured by Mitsubishi Chemical Corporation; "DTDA" manufactured by Sumitomo Seika Chemicals Co., Ltd., etc.

[0286] -Benzoxazine resin-

[0287] When combined with an epoxy resin, the benzoxazine resin can react with the epoxy resin to cure the resin composition, and thus is sometimes referred to as a "benzoxazine-based curing agent". Specific examples of the benzoxazine resin include "JBZ-OP100D", "ODA-BOZ" manufactured by JFE Chemical Corporation; "HFB2006M" manufactured by Showa Highpolymer Co., Ltd.; "P-d", "F-a" manufactured by Shikoku Kasei Kogyo Co., Ltd., etc.

[0288] When combined with an epoxy resin, the thiol resin can react with the epoxy resin to cure the resin composition, and thus is sometimes referred to as a "thiol-based curing agent". As the thiol resin, for example, trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetra(3-mercaptobutyrate), tris(3-mercaptopropyl)isocyanurate, etc. can be cited.

[0289] -Terminal double bond resin-

[0290] The terminal double bond resin is a radically polymerizable resin having one or more (preferably two or more) carbon-carbon double bond-containing ethylenically unsaturated groups in one molecule, or a radically polymerizable group containing an ethylenically unsaturated bond at the molecular end. As the radically polymerizable group, for example, one or more selected from vinyl, propenyl (1-propenyl), allyl (2-propenyl), styryl, vinylphenyl, acryloyl, and methacryloyl can be cited. Among them, from the viewpoint of more effectively enjoying the effects of the present invention, one or more selected from vinyl, allyl, and styryl are preferred. Among them, from the viewpoint of easily enjoying the effects of the present invention, the terminal double bond resin is preferably an allyl resin, a vinyl resin, or a styryl resin.

[0291] The allyl resin is, for example, a compound having one or more, preferably two or more, allyl groups. As the allyl resin, for example, aromatic carboxylic acid allyl ester compounds such as diallyl diphenate, triallyl trimellitate, diallyl phthalate, diallyl isophthalate, diallyl terephthalate, diallyl 2,6-naphthalenedicarboxylate, and diallyl 2,3-naphthalenedicarboxylate can be cited; isocyanuric acid allyl ester compounds such as 1,3,5-triallyl isocyanurate and 1,3-diallyl-5-glycidyl isocyanurate; aromatic allyl compounds containing an epoxy group such as 2,2-bis[3-allyl-4-(glycidyloxy)phenyl]propane; aromatic allyl compounds containing a benzoxazine such as bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane; aromatic allyl compounds containing an ether such as 1,3,5-triallyl ether benzene; allyl silane compounds such as diallyl diphenylsilane, etc. As commercially available products of allyl-based radically polymerizable compounds, for example: "TAIC" (1,3,5-triallyl isocyanurate) manufactured by Nippon Kasei Co., Ltd., "DAD" (diallyl diphenate) manufactured by Nisshoku Techno Fine Chemical Co., Ltd., "TRIAM-705" (triallyl trimellitate) manufactured by Fujifilm Wako Pure Chemical Corporation, the product name "DAND" (diallyl 2,3-naphthalenedicarboxylate) manufactured by Nisshoku Techno Fine Chemical Co., Ltd., "ALP-d" (bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane) manufactured by Shikoku Kasei Kogyo Co., Ltd., "RE-810NM" (2,2-bis[3-allyl-4-(glycidyloxy)phenyl]propane) manufactured by Nippon Kayaku Co., Ltd., "DA-MGIC" (1,3-diallyl-5-glycidyl isocyanurate) manufactured by Shikoku Kasei Kogyo Co., Ltd., etc.

[0292] Examples of the vinyl resin include triallyl isocyanurate and other triallyl isocyanurate compounds, polybutadiene resins having repeating units of 1,2-butadiene, cis-1,4-butadiene, and trans-1,4-butadiene, and vinylbenzyl compounds such as styrene and divinylbenzene having a vinylbenzyl group in the molecule.

[0293] As the styryl resin, as long as it has one or more (preferably two or more) styryl groups or vinylphenyl groups in one molecule, its type is not particularly limited, and it can be a monomer or an oligomer. Examples of the styryl resin include styryl resins such as "OPE-2St", "OPE-2St 1200", and "OPE-2St 2200" (all manufactured by Mitsubishi Gas Chemical Company). As the styryl resin, in addition to styrene monomer, examples also include homopolymers of aromatic divinyl compounds such as divinylbenzene, 2,4-divinyltoluene, 2,6-divinylnaphthalene, 1,4-divinylnaphthalene, 4,4'-divinylbiphenyl, 1,2-bis(4-vinylphenyl)ethane, 2,2-bis(4-vinylphenyl)propane, and bis(4-vinylphenyl)ether, or copolymers of these aromatic divinyl compounds and aromatic monovinyl compounds such as styrene, vinyltoluene, ethylstyrene, and vinylnaphthalene.

[0294] From the viewpoint of a resin composition capable of achieving a cured product that exhibits good dielectric properties, good mechanical properties (high elongation at break), and excellent crack resistance in combination with the component (A) and the component (B), when the resin component in the resin composition is set to 100% by mass, the content of the component (C) is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, still further preferably 20% by mass or more, and the upper limit of its content is preferably 60% by mass or less, more preferably 50% by mass or less, further preferably 40% by mass or less or 35% by mass or less. Therefore, in one embodiment, when the resin component in the resin composition is set to 100% by mass, the content of the component (C) is 10% by mass or more and 50% by mass or less.

[0295] From the viewpoint of a resin composition capable of achieving a cured product having good dielectric properties, good mechanical properties (high elongation at break), and excellent crack resistance, when the resin component in the resin composition is 100% by mass, the total content of component (A), component (B), and component (C) is preferably 60% by mass or more, more preferably 70% by mass or more, still more preferably 80% by mass or more, even more preferably 85% by mass or more or 90% by mass or more, and the upper limit is not particularly limited. For example, it can be set to 99.8% by mass or less, 99.5% by mass or less, 99% by mass or less, etc.

[0296] [(D) Thermoplastic resin]

[0297] The resin composition of the present invention may contain a thermoplastic resin as component (D).

[0298] Examples of component (D) include polystyrene resin, oxazoline group-containing resin, polyimide resin, phenoxy resin, polyvinyl acetal resin, polyolefin resin, polybutadiene resin, polyamideimide resin, polyetherimide resin, polysulfone resin, polyethersulfone resin, polyphenylene ether resin, polycarbonate resin, polyetheretherketone resin, polyester resin, etc.

[0299] In one embodiment, component (D) preferably contains one or more selected from polystyrene resin, oxazoline group-containing resin, polyimide resin, and phenoxy resin, more preferably contains one or more selected from polyimide resin and phenoxy resin, and particularly preferably contains phenoxy resin. In addition, component (D) can be used alone or in combination of two or more.

[0300] Commercially available products can be used for the polystyrene resin. Examples include hydrogenated styrene-based thermoplastic elastomers "H1041", "Tuftec H1043", "Tuftec P2000", "Tuftec MP10" (manufactured by Asahi Kasei Corporation); epoxidized styrene-butadiene thermoplastic elastomers "Epofriend AT501", "CT310" (manufactured by Daicel Corporation); modified styrene-based elastomers with hydroxyl groups "SEPTON HG252" (manufactured by Kuraray Co., Ltd.); modified styrene-based elastomers with carboxyl groups "TuftecN503M", modified styrene-based elastomers with amino groups "Tuftec N501", modified styrene-based elastomers with acid anhydride groups "TuftecM1913" (manufactured by Asahi Kasei Corporation); unmodified styrene-based elastomers "SEPTON S8104" (manufactured by Kuraray Co., Ltd.), etc.

[0301] The oxazoline group-containing resin can be obtained, for example, by polymerizing addition-polymerizable oxazoline compounds (monomers containing a vinyl oxazoline skeleton) such as 2-isopropenyl-2-oxazoline, 5-methyl-2-isopropenyl-2-oxazoline, 4,4-dimethyl-2-isopropenyl-2-oxazoline, 4-methyl-2-isopropenyl-2-oxazoline, 4,4,5-trimethyl-2-isopropenyl-2-oxazoline, 2-vinyl-2-oxazoline, 5-methyl-2-vinyl-2-oxazoline, 4,4-dimethyl-2-vinyl-2-oxazoline, 4-methyl-2-vinyl-2-oxazoline, 4,4,5-trimethyl-2-vinyl-2-oxazoline, etc. If necessary, other monomers such as styrene-based monomers such as styrene, α-methylstyrene, 4-methylstyrene, 3-methylstyrene, 2-methylstyrene, 4-ethylstyrene, 4-tert-butylstyrene, p-divinylbenzene, m-divinylbenzene, etc. can be copolymerized. Specific examples of the oxazoline group-containing resin include "PX-3-RP-61" manufactured by Nippon Shokubai Co., Ltd., etc.

[0302] Specific examples of the polyimide resin include "SLK-6100" manufactured by Shin-Etsu Chemical Co., Ltd., "RIKACOAT SN20" and "RIKACOAT PN20" manufactured by Shin Nippon Rika Co., Ltd., "PIAD200" manufactured by Arakawa Chemical Co., Ltd., etc.

[0303] As the phenoxy resin, for example, a phenoxy resin having one or more skeletons selected from a bisphenol A skeleton, a bisphenol F skeleton, a bisphenol S skeleton, a bisphenol acetophenone skeleton, a novolak skeleton, a biphenyl skeleton, a fluorene skeleton, a dicyclopentadiene skeleton, a norbornene skeleton, a naphthalene skeleton, an anthracene skeleton, an adamantane skeleton, a terpene skeleton, and a trimethylcyclohexane skeleton can be mentioned. The terminal of the phenoxy resin can be any functional group such as a phenolic hydroxyl group or an epoxy group. However, the phenoxy resin does not contain substances belonging to epoxy resins.

[0304] Specific examples of the phenoxy resin include "1256" and "4250" (both are phenoxy resins containing a bisphenol A skeleton) manufactured by Mitsubishi Chemical Corporation; "YX8100" (a phenoxy resin containing a bisphenol S skeleton) manufactured by Mitsubishi Chemical Corporation; "YX6954" (a phenoxy resin containing a bisphenol acetophenone skeleton) manufactured by Mitsubishi Chemical Corporation, "FX280" and "FX293" manufactured by Nippon Steel Chemical & Material Co., Ltd.; "YX7200B35", "YL7500BH30", "YX6954BH30", "YX7553BH30", "YL7769BH30", "YL6794", "YL7213", "YL7290", and "YL7482" manufactured by Mitsubishi Chemical Corporation, etc.

[0305] As the polyvinyl acetal resin, examples thereof include polyvinyl formal resin and polyvinyl butyral resin, and polyvinyl butyral resin is preferred. Specific examples of the polyvinyl acetal resin include S-LEC BH series, BX series (e.g., BX-5Z), KS series (e.g., KS-1), BL series, BM series, etc. manufactured by Sekisui Chemical Co., Ltd.

[0306] As the polyolefin resin, examples thereof include ethylene-based copolymer resins such as low density polyethylene, ultra-low density polyethylene, high density polyethylene, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, and ethylene-methyl acrylate copolymer; and polyolefin-based polymers such as polypropylene and ethylene-propylene block copolymer.

[0307] As the polybutadiene resin, examples thereof include resins containing a hydrogenated polybutadiene skeleton, polybutadiene resins containing a hydroxyl group, polybutadiene resins containing a phenolic hydroxyl group, polybutadiene resins containing a carboxyl group, polybutadiene resins containing an acid anhydride group, polybutadiene resins containing an epoxy group, polybutadiene resins containing an isocyanate group, polybutadiene resins containing a urethane group, polyphenylene ether-polybutadiene resins, etc.

[0308] Specific examples of the polyamideimide resin include "VYLOMAX HR11NN" and "VYLOMAX HR16NN" manufactured by Toyobo Co., Ltd. Specific examples of the polyamideimide resin also include modified polyamideimides such as "KS9100" and "KS9300" (polyamideimide containing a polysiloxane skeleton) manufactured by Resonac Co., Ltd.

[0309] Specific examples of the polyethersulfone resin include "PES5003P" etc. manufactured by Sumitomo Chemical Co., Ltd.

[0310] Specific examples of the polysulfone resin include polysulfones "P1700", "P3500", etc. manufactured by Solvay Advanced Polymers.

[0311] Specific examples of the polyphenylene ether resin include "NORYL SA90" etc. manufactured by SABIC. Specific examples of the polyetherimide resin include "Ultem" etc. manufactured by GE.

[0312] As the polycarbonate resin, examples thereof include a carbonate resin containing a hydroxyl group, a carbonate resin containing a phenolic hydroxyl group, a carbonate resin containing a carboxyl group, a carbonate resin containing an acid anhydride group, a carbonate resin containing an isocyanate group, a carbonate resin containing a urethane group, etc. Specific examples of the polycarbonate resin include "FPC0220" manufactured by Mitsubishi Gas Chemical Company, "T6002", "T6001" (polycarbonate diol) manufactured by Asahi Kasei Corporation, "C-1090", "C-2090", "C-3090" (polycarbonate diol) manufactured by Kuraray Co., Ltd., etc. Specific examples of the polyetheretherketone resin include "Sumiploy K" manufactured by Sumitomo Chemical Company, etc.

[0313] As the polyester resin, examples thereof include polyethylene terephthalate resin, polyethylene naphthalate resin, polybutylene terephthalate resin, polybutylene naphthalate resin, polypropylene terephthalate resin, polypropylene naphthalate resin, polycyclohexanedimethylene terephthalate resin, etc.

[0314] When the resin component in the resin composition is set to 100% by mass, the content of the component (D) in the resin composition is, for example, 0% by mass or more, preferably 0.01% by mass or more, more preferably 0.1% by mass or more, still more preferably 0.5% by mass or more, 1% by mass or more, 2% by mass or more, or 3% by mass or more. The upper limit of the content is preferably 30% by mass or less, more preferably 25% by mass or less, still more preferably 20% by mass or less, 15% by mass or less, or 10% by mass or less.

[0315] [(E) Inorganic filler]

[0316] The resin composition of the present invention may contain an inorganic filler as the component (E).

[0317] Examples of the inorganic filler include silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum silicate, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium zirconate titanate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium phosphotungstate. Among these, silica is particularly suitable. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, hollow silica, etc. In addition, as silica, spherical silica is preferred. The inorganic filler may be used alone or in combination of two or more.

[0318] Examples of commercially available inorganic filler products include, for example, "SP60-05" and "SP507-05" manufactured by Nippon Steel Chemical Co., Ltd.; "YC100C", "YA050C", "YA050C-MJE", "YA010C", "SC2500SQ", "SO-C4", "SO-C2", "SO-C1" manufactured by Admatechs Co., Ltd.; "UFP-30", "DAW-03", "FB-105FD" manufactured by Denka Co., Ltd.; "Silfil NSS-3N", "Silfil NSS-4N", "Silfil NSS-5N" manufactured by Tokuyama Corporation; "Cellspheres", "MGH-005", etc. manufactured by Taiheiyo Cement Corporation.

[0319] The average particle diameter of the inorganic filler is not particularly limited, preferably 10 μm or less, more preferably 5 μm or less, still more preferably 3 μm or less, 2 μm or less, 1 μm or less, or 0.7 μm or less. The lower limit of the average particle diameter is not particularly limited, preferably 0.01 μm or more, more preferably 0.05 μm or more, still more preferably 0.07 μm or more, 0.1 μm or more, or 0.2 μm or more.

[0320] The average particle diameter of the inorganic filler can be measured by the laser diffraction / scattering method based on the Mie scattering theory. Specifically, a particle size distribution of the inorganic filler can be created on a volume basis using a laser diffraction scattering type particle size distribution measuring device, and the median diameter thereof can be measured as the average particle diameter. As the measurement sample, a sample obtained by weighing 100 mg of the inorganic filler and 10 g of methyl ethyl ketone into a vial and dispersing them ultrasonically for 10 minutes can be used. For the measurement sample, using a laser diffraction type particle size distribution measuring device, the wavelength of the light source used is set to blue and red, and the volume-based particle size distribution of the inorganic filler is measured by the flow cell method, and the average particle diameter is calculated as the median diameter from the obtained particle size distribution. Examples of the laser diffraction type particle size distribution measuring device include "LA-960" manufactured by Horiba, Ltd.

[0321] The specific surface area of the inorganic filler is not particularly limited, preferably 0.1 m 2 / g or more, more preferably 0.5 m 2 / g or more, still more preferably 1 m 2 / g or more, 3 m 2 / g or more, or 5 m 2 / g or more. The upper limit of the specific surface area is not particularly limited, preferably 100 m 2 / g or less, more preferably 80 m 2 / g or less, still more preferably 60 m 2 / g or less, 50 m 240 m or less per g 2 per g or less.

[0322] The specific surface area of the inorganic filler can be obtained as follows: According to the BET method, nitrogen is adsorbed on the surface of the sample using a specific surface area measuring device (Macsorb HM-1210 manufactured by Mountech Co., Ltd.), and the specific surface area is calculated using the BET multipoint method.

[0323] The inorganic filler is preferably surface-treated with an appropriate surface treatment agent. By performing surface treatment, the moisture resistance and dispersibility of the inorganic filler can be improved. Examples of the surface treatment agent include silane coupling agents such as vinyl-based silane coupling agents, epoxy-based silane coupling agents, styryl-based silane coupling agents, (meth)acrylic-based silane coupling agents, amino-based silane coupling agents, isocyanurate-based silane coupling agents, acylurea-based silane coupling agents, mercapto-based silane coupling agents, isocyanate-based silane coupling agents, and anhydride-based silane coupling agents; non-silane coupling-alkoxysilane compounds such as methyltrimethoxysilane and phenyltrimethoxysilane; and silazane compounds. The surface treatment agent can be used alone or in combination of two or more.

[0324] Examples of commercially available products of the surface treatment agent include "KBM403" (3-glycidoxypropyltrimethoxysilane), "KBM803" (3-mercaptopropyltrimethoxysilane), "KBE903" (3-aminopropyltriethoxysilane), "KBM573" (N-phenyl-3-aminopropyltrimethoxysilane), "SZ-31" (hexamethyldisilazane), etc., manufactured by Shin-Etsu Chemical Co., Ltd.

[0325] From the viewpoint of improving the dispersibility of the inorganic filler, the degree of surface treatment with the surface treatment agent preferably falls within a specified range. Specifically, it is preferred that 100% by mass of the inorganic filler is preferably surface-treated with 0.2 to 5% by mass of the surface treatment agent.

[0326] The degree of surface treatment with the surface treatment agent can be evaluated based on the carbon amount per unit surface area of the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, the carbon amount per unit surface area of the inorganic filler is preferably 0.02 mg / m 2 or more, more preferably 0.1 mg / m 2 or more, and further preferably 0.2 mg / m 2 or more. On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition and the melt viscosity in the sheet form, it is preferably 1.0 mg / m 2Hereinafter, it is more preferably 0.8 mg / m 2 Hereinafter, it is further preferably 0.5 mg / m 2 Hereinafter. The carbon amount per unit surface area of the component (E) can be measured after cleaning the surface-treated inorganic filler with a solvent (e.g., methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent is added to the inorganic filler surface-treated with a surface treatment agent, and ultrasonic cleaning is performed at 25°C for 5 minutes. After removing the supernatant and drying the solid component, a carbon analyzer can be used to measure the carbon amount per unit surface area of the inorganic filler. As the carbon analyzer, “EMIA-320V” manufactured by Horiba, Ltd. etc. can be used.

[0327] From the viewpoint of a resin composition capable of achieving a cured product having good dielectric properties, good mechanical properties (high elongation at break), and excellent crack resistance in combination with the components (A) to (C), when the non-volatile components in the resin composition are set to 100% by mass, the content of the component (E) is preferably 50% by mass or more, more preferably 60% by mass, further preferably 70% by mass or more, and the upper limit of its content is preferably 85% by mass or less, more preferably 80% by mass or less.

[0328] [(F) Radical polymerization initiator]

[0329] The resin composition of the present invention may contain a radical polymerization initiator as the component (F).

[0330] Examples of the component (F) include a thermal polymerization initiator that generates radicals upon heating and a photo-polymerization initiator that generates radicals upon light irradiation. Among them, from the viewpoint of being able to more enjoy the effects of the present invention, a thermal polymerization initiator is preferred. The component (F) can be used alone or in any combination of two or more.

[0331] Examples of the component (F) include peroxide-based radical polymerization initiators and azo-based radical polymerization initiators. Among them, peroxide-based radical polymerization initiators are preferred.

[0332] As peroxide-based radical polymerization initiators, examples include peroxide compounds such as 1,1,3,3-tetramethylbutyl hydroperoxide; dialkyl peroxide compounds such as tert-butyl cumyl peroxide, di-tert-butyl peroxide, di-tert-hexyl peroxide, dicumyl peroxide, 1,4-bis(1-tert-butylperoxy-1-methylethyl)benzene, 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane; diacyl peroxide compounds such as dilauroyl peroxide, didecanoyl peroxide, dicyclohexyl peroxydicarbonate, bis(4-tert-butylcyclohexyl) peroxydicarbonate; peroxyester compounds such as tert-butyl peroxyacetate, tert-butyl peroxybenzoate, tert-butyl peroxyisopropyl monocarbonate, tert-butyl peroxy-2-ethylhexanoate, tert-butyl peroxypivalate, tert-hexyl peroxyisopropyl monocarbonate, tert-butyl laurate, 1,1-dimethylpropyl 2-ethylperoxyhexanoate, tert-butyl 2-ethylperoxyhexanoate, tert-butyl 3,5,5-trimethylperoxyhexanoate, tert-butyl peroxy-2-ethylhexyl monocarbonate, tert-butyl peroxymaleate, etc.

[0333] As azo-based radical polymerization initiators, examples include azonitrile compounds such as 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonitrile), 1-[(1-cyano-1-methylethyl)azo]formamide, 2-phenylazo-4-methoxy-2,4-dimethylvaleronitrile; azoamide compounds such as 2,2'-azobis[2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide], 2,2'-azobis[2-methyl-N-[1,1-bis(hydroxymethyl)ethyl]propionamide], 2,2'-azobis[2-methyl-N-[2-(1-hydroxybutyl)]propionamide], 2,2'-azobis[2-methyl-N-(2-hydroxyethyl)propionamide], 2,2'-azobis(2-methylpropionamide) dihydrate, 2,2'-azobis[N-(2-propenyl)-2-methylpropionamide], 2,2'-azobis(N-butyl-2-methylpropionamide), 2,2'-azobis(N-cyclohexyl-2-methylpropionamide); alkyl azo compounds such as 2,2'-azobis(2,4,4-trimethylpentane), 2,2'-azobis(2-methylpropane), etc.

[0334] Examples of commercially available products as component (F) include, for example, "PERBUTYL C", "PERBUTYL A", "PERBUTYL P", "PERBUTYL L", "PERBUTYL O", "PERBUTYL ND", "PERBUTYL Z", "PERBUTYLI", "PERCUMYL P", "PERCUMYL D", "PERHEXYL D", "PERHEXYL A", "PERHEXYL I", "PERHEXYLZ", "PERHEXYL ND", "PERHEXYL O", "PERHEXYL PV", etc. manufactured by NOF Corporation.

[0335] The content of component (F) in the resin composition is not particularly limited. When the resin component in the resin composition is set to 100% by mass, it is preferably 10% by mass or less, more preferably 5% by mass or less, further preferably 3% by mass or less, and still further preferably 1.5% by mass or less. The lower limit of the content is not particularly limited. When the resin component in the resin composition is set to 100% by mass, for example, it can be 0% by mass or more, preferably 0.01% by mass or more, more preferably 0.05% by mass or more, further preferably 0.1% by mass or more, 0.3% by mass or more, 0.5% by mass or more, or 0.8% by mass or more, etc.

[0336] [(G) Curing accelerator]

[0337] The resin composition of the present invention may contain a curing accelerator as component (G).

[0338] Examples of component (G) include, for example, phosphorus-based curing accelerators, amine-based curing accelerators, imidazole-based curing accelerators, guanidine-based curing accelerators, metal-based curing accelerators, etc. Preferred are amine-based curing accelerators, imidazole-based curing accelerators, and metal-based curing accelerators, and more preferably any one of amine-based curing accelerators and imidazole-based curing accelerators. Component (B) can be used alone or in combination of two or more.

[0339] Examples of phosphorus-based curing accelerators include, for example, triphenylphosphine, phosphonium borate compounds, tetraphenylphosphonium tetraphenylborate, n-butylphosphonium tetraphenylborate, tetrabutylphosphonium caprylate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, butyltriphenylphosphonium thiocyanate, etc. Preferred are triphenylphosphine and tetrabutylphosphonium caprylate.

[0340] Examples of amine-based curing accelerators include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, 1,8-diazabicyclo[5.4.0]undecene, etc. Preferred are 4-dimethylaminopyridine and 1,8-diazabicyclo[5.4.0]undecene.

[0341] Examples of imidazole-based curing accelerators include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium trimesate, 1-cyanoethyl-2-phenylimidazolium trimesate, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-undecylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine isocyanuric acid adduct, 2-phenylimidazole isocyanuric acid adduct, 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, 2-phenylimidazoline and other imidazole compounds, and adducts of imidazole compounds and epoxy resins. Preferred are 2-ethyl-4-methylimidazole and 1-benzyl-2-phenylimidazole.

[0342] As the imidazole-based curing accelerator, commercially available products can be used, and examples include "P200-H50" manufactured by Mitsubishi Chemical Corporation and "1B2PZ" manufactured by Shikoku Kasei Kogyo Co., Ltd.

[0343] As guanidine-based curing accelerators, examples include dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1-(o-tolyl)guanidine, dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecylbiguanide, 1,1-dimethylbiguanide, 1,1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, 1-(o-tolyl)biguanide, etc. Preferred are dicyandiamide and 1,5,7-triazabicyclo[4.4.0]dec-5-ene.

[0344] As metal-based curing accelerators, examples include organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, tin, etc. Specific examples of organometallic complexes include organocobalt complexes such as cobalt(II) acetylacetonate, cobalt(III) acetylacetonate, organocopper complexes such as copper(II) acetylacetonate, organozinc complexes such as zinc(II) acetylacetonate, organoiron complexes such as iron(III) acetylacetonate, organonickel complexes such as nickel(II) acetylacetonate, organomanganese complexes such as manganese(II) acetylacetonate, etc. Examples of organometallic salts include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, zinc stearate, etc.

[0345] The content of the component (G) in the resin composition is not particularly limited. When the resin component in the resin composition is set to 100% by mass, it is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, preferably 2% by mass or less, and more preferably 1% by mass or less.

[0346] <Other additives>

[0347] In the resin composition of the present invention, in addition to the above components, other additives may be further included as optional components. Examples of other additives include: organometallic compounds such as organic copper compounds, organic zinc compounds, and organic cobalt compounds; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; homogenizers such as organosilicon-based homogenizers and acrylic polymer-based homogenizers; thickeners such as Benton and montmorillonite; defoamers such as organosilicon-based defoamers, acrylic-based defoamers, fluorine-based defoamers, and vinyl resin-based defoamers; ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers; adhesion improvers such as ureasilane; adhesion imparting agents such as triazole-based adhesion imparting agents, tetrazole-based adhesion imparting agents, and triazine-based adhesion imparting agents; antioxidants such as hindered phenol-based antioxidants; fluorescent brighteners such as stilbene derivatives; surfactants such as fluorine-based surfactants and organosilicon-based surfactants; flame retardants such as phosphorus-based flame retardants (e.g., phosphate compounds, phosphazene compounds, phosphonic acid compounds, red phosphorus), nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic flame retardants (e.g., antimony trioxide); dispersants such as phosphate ester-based dispersants, polyoxyalkylene-based dispersants, acetylene-based dispersants, organosilicon-based dispersants, anionic dispersants, and cationic dispersants; stabilizers such as borate / ester-based stabilizers, titanate / ester-based stabilizers, aluminate / ester-based stabilizers, zirconate / ester-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, and carboxylic anhydride-based stabilizers; photoinitiator aids such as tertiary amines; photosensitizers such as pyrazolines, anthracenes, coumarins, xanthones, and thioxanthones.

[0348] These other additives can be used individually as one kind, or two or more kinds can be used in combination.

[0349] [Solvent]

[0350] In addition to containing the above-mentioned non-volatile components, the resin composition of the present invention may also contain a solvent as a volatile component. As the solvent, known solvents can be appropriately used, and the type thereof is not particularly limited, and an organic solvent is preferably used. Examples of the solvent include ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, and γ-butyrolactone; ether solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, diphenyl ether, and anisole; alcohol solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; ether ester solvents such as 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl diglycol acetate, γ-butyrolactone, and methyl methoxypropionate; ester alcohol solvents such as methyl lactate, ethyl lactate, and methyl 2-hydroxyisobutyrate; ether alcohol solvents such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, and diethylene glycol monobutyl ether (butyl carbitol); amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; nitrile solvents such as acetonitrile and propionitrile; aliphatic hydrocarbon solvents such as hexane, cyclopentane, cyclohexane, and methylcyclohexane; aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene, etc. (J) The solvent can be used alone or in combination of two or more in any ratio.

[0351] The amount of the solvent is not particularly limited. When all the components in the resin composition are set to 100% by mass, for example, it can be 60% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, 15% by mass or less, 10% by mass or less, etc., or it can be 0% by mass.

[0352] [Method for manufacturing resin composition]

[0353] The resin composition of the present invention can be manufactured, for example, by mixing the components that can be contained in the resin composition. The above-mentioned components can be mixed partially or all at the same time, or can be mixed sequentially. During the mixing of each component, the temperature can be appropriately set, so heating and / or cooling can be carried out temporarily or continuously. In addition, during the mixing of each component, stirring or oscillation can be carried out.

[0354] [Properties of resin composition]

[0355] The cured product of the resin composition of the present invention can have a low dielectric loss tangent. Therefore, when an insulating layer is formed of the cured product, an insulating layer with a low dielectric loss tangent can be obtained. The dielectric loss tangent of the cured product of the resin composition is preferably 0.003 or less, more preferably 0.0028 or less, and still more preferably 0.0025 or less. The lower limit is not particularly limited, but can be set to 0.0001 or more, etc. The dielectric loss tangent can be measured by the method described in the examples below.

[0356] The cured product of the resin composition of the present invention exhibits the characteristic of a high elongation at break. Therefore, when an insulating layer is formed of the cured product, an insulating layer with excellent mechanical strength can be obtained. The elongation at break of the cured product of the resin composition is preferably 1.4% or more, more preferably 1.5% or more, 1.6% or more, 1.8% or more, or 2% or more. The upper limit value is not particularly limited, and can be set to 10% or less, for example. The elongation at break can be measured by the method described in the examples below.

[0357] The cured product of the resin composition of the present invention exhibits the characteristic of excellent crack resistance. Therefore, when an insulating layer is formed of the cured product, an insulating layer with excellent crack resistance can be obtained. Specifically, the resin composition is laminated on an inner layer substrate on which a wiring pattern is formed, and thermally cured to obtain a cured product. The surface of the cured product is roughened to obtain a specimen. Among 100 parts on the pattern of the inner layer substrate of the specimen, it is confirmed whether cracks are generated on the surface along the pattern shape, the number of parts on the pattern where no cracks are generated is counted, and the ratio of the parts where no cracks are generated among 100 parts is calculated as the "yield". At this time, the yield is preferably 40% or more, more preferably 60% or more, and still more preferably 80% or more. The crack resistance can be measured by the method described in the examples below.

[0358] [Use of the resin composition]

[0359] The resin composition of the present invention can be suitably used as a resin composition for forming an insulating layer of a printed wiring board (resin composition for insulating layer of printed wiring board), and can be more suitably used as a resin composition for forming an interlayer insulating layer of a printed wiring board (resin composition for interlayer insulating layer of printed wiring board). The resin composition of the present invention can also be suitably used when the printed wiring board is a component-embedded circuit board. The resin composition of the present invention can also be suitably used as a resin composition for forming an insulating layer of a redistribution substrate of a semiconductor package (resin composition for insulating layer of redistribution substrate). It should be noted that in the present invention, the printed wiring board and the redistribution substrate are collectively referred to as "circuit board", and therefore, the resin composition of the present invention can be appropriately used as an insulating layer of a circuit board.

[0360] The resin composition of the present invention can further be widely used in applications that require resin compositions, such as sheet-like laminated materials such as resin sheets and prepregs, solder resists, underfill materials, chip bonding materials, via filling resins, encapsulation resins, and component-embedded resins.

[0361] [Sheet-like laminated material]

[0362] The resin composition can be used by coating it in a varnish state, but it is industrially suitable to be used in the form of a sheet-like laminated material containing the resin composition.

[0363] As the sheet-like laminated material, resin sheets and prepregs shown below are preferred.

[0364] In one embodiment, the resin sheet includes a support and a resin composition layer provided on the support. The resin composition layer is formed of the above resin composition. Therefore, the resin composition layer generally contains the resin composition and preferably contains only the resin composition.

[0365] From the viewpoints of thinning and providing a cured product with excellent insulation even when thin by the resin composition, the thickness of the resin composition layer is preferably 50 μm or less, more preferably 40 μm or less. The lower limit of the thickness of the resin composition layer is not particularly limited and can be 5 μm or more, 10 μm or more, etc.

[0366] Examples of the support include a thermoplastic resin film, a metal foil, and a release paper, and a thermoplastic resin film and a metal foil are preferred.

[0367] When using a thermoplastic resin film as the support, examples of the thermoplastic resin include polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polycarbonate (PC), acrylic polymers such as polymethyl methacrylate (PMMA), cyclic polyolefins, triacetyl cellulose (TAC), polyether sulfide (PES), polyether ketone, and polyimide. Among them, polyethylene terephthalate and polyethylene naphthalate are preferred, and inexpensive polyethylene terephthalate is particularly preferred.

[0368] When using a metal foil as the support, examples of the metal foil include a copper foil and an aluminum foil, and a copper foil is preferred. As the copper foil, a foil formed of single metal of copper or a foil formed of an alloy of copper and other metals (for example, tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) can be used.

[0369] For the support, the surface that is joined to the resin composition layer can be subjected to matte treatment, corona treatment, or antistatic treatment.

[0370] As the support, a support with a release layer can be used, which has a release layer on the surface joined to the resin composition layer. As the release agent used in the release layer of the support with a release layer, for example, one or more release agents selected from alkyd resins, polyolefin resins, polyurethane resins, and silicone resins can be cited. Commercially available products can be used as the support with a release layer, and examples include: PET films having a release layer mainly composed of an alkyd resin-based release agent, such as "SK-1", "AL-5", "AL-7" manufactured by Lintec Corporation, "LUMIRRORT60" manufactured by Toray Industries, Inc., "Purex" manufactured by Teijin Limited, "Unipeel" manufactured by UNITIKA Ltd., etc.

[0371] The thickness of the support is not particularly limited, and preferably ranges from 5 μm to 75 μm, more preferably from 10 μm to 60 μm. It should be noted that when using a support with a release layer, it is preferable that the overall thickness of the support with a release layer is within the above range.

[0372] When using a metal foil as the support, a metal foil with a support substrate can be used, in which a peelable support substrate is adhered to a thin metal foil. In one embodiment, the metal foil with a support substrate includes a support substrate, a release layer provided on the support substrate, and a metal foil provided on the release layer. When using a metal foil with a support substrate as the support, the resin composition layer is provided on the metal foil.

[0373] In the metal foil with a support substrate, the material of the support substrate is not particularly limited, and examples include copper foil, aluminum foil, stainless steel foil, titanium foil, copper alloy foil, etc. When using a copper foil as the support substrate, it can be an electrolytic copper foil or a rolled copper foil. In addition, for the release layer, if the metal foil can be peeled from the support substrate, there is no particular limitation, and examples include alloy layers of elements selected from Cr, Ni, Co, Fe, Mo, Ti, W, P; organic films, etc.

[0374] In the metal foil with a support substrate, as the material of the metal foil, for example, copper foil or copper alloy foil is preferably used.

[0375] In the metal foil with a support substrate, the thickness of the support substrate is not particularly limited, and preferably ranges from 10 μm to 150 μm, more preferably from 10 μm to 100 μm. In addition, the thickness of the metal foil can be set, for example, in the range of 0.1 μm to 10 μm.

[0376] In one embodiment, the resin sheet may further include an arbitrary layer as needed. As the arbitrary layer, for example, a protective film selected according to the support may be provided on the surface of the resin composition layer that is not joined to the support (i.e., the surface on the side opposite to the support). The thickness of the protective film is not particularly limited, and is, for example, 1 μm to 40 μm. By laminating the protective film, it is possible to suppress the adhesion of dust and the like to the surface of the resin composition layer or damage to the surface of the resin composition layer.

[0377] The resin sheet can be manufactured, for example, as follows: directly using a liquid (varnish-like) resin composition, or preparing a liquid (varnish-like) resin composition by dissolving the resin composition in a solvent, and coating the liquid (varnish-like) resin composition on a support using a die coater or the like, and then drying to form a resin composition layer.

[0378] As the solvent, the same solvents as those described as the components of the resin composition can be cited. The solvent can be used alone or in combination of two or more.

[0379] Drying can be carried out by methods such as heating and hot air blowing. The drying conditions are not particularly limited, and drying is performed such that the content of the solvent in the resin composition layer usually becomes 10% by mass or less, preferably 5% by mass or less. The drying conditions also vary depending on the boiling point of the solvent in the resin composition. For example, in the case of using a resin composition containing 30% to 60% by mass of the solvent, a resin composition layer can be formed by drying at 50°C to 150°C for 3 minutes to 10 minutes.

[0380] The resin sheet can be wound into a roll for storage. When the resin sheet has a protective film, it can usually be used by peeling off the protective film.

[0381] In one embodiment, the prepreg is formed by impregnating the resin composition of this embodiment in a sheet-like fiber substrate.

[0382] As the sheet-like fiber substrate used in the prepreg, for example, materials commonly used as prepreg substrates such as glass cloth, aramid non-woven fabric, and liquid crystal polymer non-woven fabric can be used. From the viewpoint of thinning, the thickness of the sheet-like fiber substrate is preferably 50 μm or less, more preferably 40 μm or less, further preferably 30 μm or less, and particularly preferably 20 μm or less. The lower limit of the thickness of the sheet-like fiber substrate is not particularly limited. Usually, it is 10 μm or more.

[0383] The prepreg can be manufactured by methods such as a hot melt method and a solvent method.

[0384] The thickness of the prepreg can be in the same range as the resin composition layer in the above-mentioned resin sheet.

[0385] The sheet-like laminated material can be suitably used for forming an insulating layer of a printed wiring board (for the insulating layer of a printed wiring board), and can be more suitably used for forming an interlayer insulating layer of a printed wiring board (for the interlayer insulating layer of a printed wiring board). The sheet-like laminated material of the present invention can also be suitably used for forming an insulating layer of a rewiring substrate of a semiconductor package (for the insulating layer of a rewiring substrate). That is, the sheet-like laminated material of the present invention can be suitably used as an insulating layer of a circuit board.

[0386] [Circuit board]

[0387] An insulating layer of a circuit board can be formed using the resin composition of the present invention. The present invention also provides the circuit board, that is, a circuit board including an insulating layer formed of a cured product of the resin composition of the present invention.

[0388] <Printed wiring board>

[0389] In one embodiment, the circuit board of the present invention is a printed wiring board.

[0390] The printed wiring board can be manufactured, for example, using the above resin sheet and by a method including the following steps (I) and (II).

[0391] (I) A step of laminating a resin sheet on an inner layer substrate in such a manner that the resin composition layer of the resin sheet is joined to the inner layer substrate

[0392] (II) A step of curing (for example, thermally curing) the resin composition layer to form an insulating layer.

[0393] The "inner layer substrate" used in step (I) refers to a member that becomes the substrate of a printed wiring board, and examples thereof include a glass epoxy substrate, a metal substrate, a polyester substrate, a polyimide substrate, a BT resin substrate, and a thermosetting polyphenylene ether substrate. In addition, the substrate may have a conductor layer on one or both sides thereof, and the conductor layer may be pattern-processed. An inner layer substrate having a conductor layer (circuit) formed on one or both sides of the substrate is sometimes referred to as an "inner layer circuit substrate". In addition, an intermediate product to be further formed with an insulating layer and / or a conductor layer when manufacturing a printed wiring board is also included in the "inner layer substrate" as used in the present invention. When the printed wiring board is a component-embedded circuit board, an inner layer substrate having components embedded therein can be used.

[0394] The lamination of the inner substrate and the resin sheet can be carried out, for example, by thermocompression bonding the resin sheet to the inner substrate from the support side. As a member for thermocompression bonding the resin sheet to the inner substrate (hereinafter also referred to as "thermocompression bonding member"), for example, a heated metal plate (such as a SUS end plate), or a metal roll (SUS roll) can be cited. It should be noted that the thermocompression bonding member can be directly pressed against the resin sheet, or can be pressed through an elastic material such as heat-resistant rubber so that the resin sheet fully follows the surface unevenness of the inner substrate.

[0395] The lamination of the inner substrate and the resin sheet can be carried out by a vacuum lamination method. In the vacuum lamination method, the thermocompression bonding temperature is preferably in the range of 60°C to 160°C, more preferably in the range of 80°C to 140°C, the thermocompression bonding pressure is preferably in the range of 0.098 MPa to 1.77 MPa, more preferably in the range of 0.29 MPa to 1.47 MPa, and the thermocompression bonding time is preferably in the range of 20 seconds to 400 seconds, more preferably in the range of 30 seconds to 300 seconds. The lamination is preferably carried out under reduced pressure conditions of 26.7 hPa or less.

[0396] The lamination can be carried out by a commercially available vacuum laminator. As a commercially available vacuum laminator, for example, a vacuum pressure type laminator manufactured by Meiki Seisakusho Co., Ltd., a vacuum coater manufactured by Nikko-Materials Co., Ltd., a batch type vacuum pressure laminator, etc. can be cited.

[0397] After the lamination, for example, the thermocompression bonding member can be pressed from the support side under normal pressure (atmospheric pressure) to carry out the smoothing treatment of the laminated resin sheet. The pressing conditions for the smoothing treatment can be set to the same conditions as the thermocompression bonding conditions for the above lamination. The smoothing treatment can be carried out by a commercially available laminator. It should be noted that the lamination and the smoothing treatment can be continuously carried out using the above-mentioned commercially available vacuum laminator.

[0398] The support can be removed between process (I) and process (II), or can be removed after process (II). It should be noted that in the case of using a metal foil as the support, the conductor layer can be formed without peeling the support and using the metal foil. In addition, in the case of using a metal foil with a support substrate as the support, the support substrate (and the release layer) can be peeled off. Moreover, a conductor layer can be formed using a metal foil.

[0399] In process (II), the resin composition layer is cured (for example, thermally cured) to form an insulating layer formed of a cured product of the resin composition. The curing conditions of the resin composition layer are not particularly limited, and the conditions generally used when forming an insulating layer of a printed wiring board can be used.

[0400] For example, the thermal curing conditions of the resin composition layer vary depending on the type of the resin composition and the like. In one embodiment, the curing temperature is preferably 140°C to 250°C, more preferably 150°C to 240°C, and still more preferably 160°C to 230°C. The curing time can be preferably set to 5 minutes to 240 minutes, more preferably set to 10 minutes to 150 minutes, and still more preferably set to 15 minutes to 120 minutes.

[0401] Before thermally curing the resin composition layer, the resin composition layer can be preheated at a temperature lower than the curing temperature. For example, before thermally curing the resin composition layer, the resin composition layer can be preheated at a temperature of 50°C to 140°C, preferably 60°C to 135°C, more preferably 70°C to 130°C for 5 minutes or more, preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, and still more preferably 15 minutes to 100 minutes.

[0402] When manufacturing a printed wiring board, the steps of (III) opening holes in the insulating layer, (IV) roughening the insulating layer, and (V) forming a conductor layer can be further implemented. These steps (III) to (V) can be implemented according to various methods well-known to those skilled in the art used in the manufacture of printed wiring boards. It should be noted that when removing the support after step (II), the removal of the support can be implemented between step (II) and step (III), between step (III) and step (IV), or between step (IV) and step (V). In addition, if necessary, the formation of the insulating layer and the conductor layer of steps (I) to (V) can be repeatedly implemented to form a multilayer wiring board.

[0403] In other embodiments, the printed wiring board of the present invention can be manufactured using the above prepreg. The manufacturing method is basically the same as that in the case of using a resin sheet.

[0404] Step (III) is a step of opening holes in the insulating layer, whereby holes such as vias and through holes can be formed in the insulating layer. Step (III) can be implemented using, for example, a drill bit, a laser, a plasma, etc. according to the composition of the resin composition used for forming the insulating layer. The size and shape of the holes can be appropriately determined according to the design of the printed wiring board.

[0405] Step (IV) is a step of roughening the insulating layer. Generally, in this step (IV), the removal of contamination (decontamination) is also performed. The steps and conditions of the roughening treatment are not particularly limited, and known steps and conditions generally used when forming the insulating layer of a printed wiring board can be adopted. For example, the insulating layer can be roughened by sequentially performing a swelling treatment using a swelling liquid, a roughening treatment using an oxidant, and a neutralization treatment using a neutralizing liquid.

[0406] The swelling liquid used in the roughening treatment is not particularly limited, and examples thereof include an alkaline solution and a surfactant solution. An alkaline solution is preferred, and as the alkaline solution, a sodium hydroxide solution and a potassium hydroxide solution are more preferred. Examples of commercially available swelling liquids include "Swelling Dip Securiganth P" and "Swelling Dip Securiganth SBU" manufactured by Atotech Japan Co., Ltd. The swelling treatment using the swelling liquid is not particularly limited. For example, it can be carried out by immersing the insulating layer in the swelling liquid at 30°C to 90°C for 1 minute to 20 minutes. From the viewpoint of suppressing the swelling of the resin of the insulating layer to an appropriate level, it is preferred to immerse the insulating layer in the swelling liquid at 40°C to 80°C for 5 minutes to 15 minutes.

[0407] The oxidizing agent used in the roughening treatment is not particularly limited, and examples thereof include an alkaline permanganic acid solution in which potassium permanganate or sodium permanganate is dissolved in an aqueous solution of sodium hydroxide. The roughening treatment using an oxidizing agent such as an alkaline permanganic acid solution is preferably carried out by immersing the insulating layer in the oxidizing agent solution heated to 60°C to 100°C for 10 minutes to 30 minutes. In addition, the concentration of the permanganate in the alkaline permanganic acid solution is preferably 5% by mass to 10% by mass. Examples of commercially available oxidizing agents include alkaline permanganic acid solutions such as "Concentrate Compact CP", "ConcentrateCompactP", and "Dosing Solution Securiganth P" manufactured by Atotech Japan Co., Ltd.

[0408] In addition, the neutralizing liquid used in the roughening treatment is preferably an acidic aqueous solution, and examples of commercially available products include "Reduction Solution Securiganth P" manufactured by Atotech Japan Co., Ltd.

[0409] The treatment using the neutralizing liquid can be carried out by immersing the treated surface that has completed the roughening treatment using the oxidizing agent in the neutralizing liquid at 30°C to 80°C for 5 minutes to 30 minutes. From the viewpoint of operability and the like, a method of immersing the object that has completed the roughening treatment using the oxidizing agent in the neutralizing liquid at 40°C to 70°C for 5 minutes to 20 minutes is preferred.

[0410] Step (V) is a step of forming a conductor layer, which forms a conductor layer on an insulating layer. There is no particular limitation on the conductor material used for the conductor layer. In a suitable embodiment, the conductor layer contains one or more metals selected from the group consisting of gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. The conductor layer may be a single-metal layer or an alloy layer. As the alloy layer, for example, a layer formed of an alloy of two or more metals selected from the above group (for example, nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy) can be cited. Among them, from the viewpoints of the versatility of forming the conductor layer, cost, ease of patterning, etc., a single-metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel-chromium alloy, copper-nickel alloy, or copper-titanium alloy is preferred, a single-metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel-chromium alloy is more preferred, and a single-metal layer of copper is further preferred.

[0411] The conductor layer may have a single-layer structure or a multilayer structure formed by laminating two or more single-metal layers or alloy layers formed of different metals or alloys. When the conductor layer has a multilayer structure, the layer in contact with the insulating layer is preferably a single-metal layer of chromium, zinc, or titanium, or an alloy layer of nickel-chromium alloy.

[0412] The thickness of the conductor layer depends on the design of the desired printed wiring board and is usually 3 μm to 35 μm, preferably 5 μm to 30 μm.

[0413] In one embodiment, the conductor layer can be formed by plating. From the viewpoint of easily forming fine wirings, it is preferably formed by the semi-additive method. Examples of forming the conductor layer by the semi-additive method are shown below.

[0414] First, a plating seed layer is formed on the surface of the insulating layer by electroless plating. Then, on the formed plating seed layer, a mask pattern is formed corresponding to the desired wiring pattern so that a part of the plating seed layer is exposed. After a metal layer is formed on the exposed plating seed layer by electroplating, the mask pattern is removed. Then, the unnecessary plating seed layer is removed by etching or the like, and a conductor layer having the desired wiring pattern can be formed.

[0415] In other embodiments, the conductor layer can be formed using a metal foil. In the case of forming the conductor layer using a metal foil, step (V) is suitably carried out between step (I) and step (II). For example, after step (I), the support is removed, and a metal foil is laminated on the surface of the exposed resin composition layer. The lamination of the resin composition layer and the metal foil can be carried out by a vacuum lamination method. The lamination conditions can be the same as those described for step (I). Next, step (II) is carried out to form the insulating layer. Then, using the metal foil on the insulating layer, a conductor layer having a desired wiring pattern can be formed by a known technique such as a modified semi-additive method.

[0416] The metal foil can be manufactured by known methods such as an electrolytic method or a rolling method, for example. As commercially available products of the metal foil, for example, HLP foil, JXUT-III foil manufactured by JX Metals Co., Ltd., 3EC-III foil, TP-III foil manufactured by Mitsui Mining & Smelting Co., Ltd., etc. can be cited.

[0417] Alternatively, in the case of using a metal foil or a metal foil with a support substrate as the support of the resin sheet, as described above, the metal foil can be used to form the conductor layer.

[0418] <Rewiring Substrate of Semiconductor Package>

[0419] In one embodiment, the circuit substrate of the present invention is a rewiring substrate (rewiring layer) of a semiconductor package. Hereinafter, it will be described according to the manufacturing method of the semiconductor package.

[0420] In the semiconductor package, as the insulating layer of the rewiring substrate, an insulating layer formed from a cured product of the resin composition of the present invention is included. It should be noted that the semiconductor package may also include a sealing layer formed from a cured product of the resin composition of the present invention.

[0421] The semiconductor package can be manufactured, for example, using the resin composition and resin sheet of the present invention and by a method including the following steps (1) to (6). In order to form the rewiring formation layer (for forming the insulating layer of the rewiring substrate) in step (5) or the sealing layer in step (3), it is only necessary to use the resin composition and resin sheet of the present invention. Hereinafter, an example of forming the rewiring formation layer and the sealing layer using the resin composition and resin sheet is shown, but the techniques for forming the rewiring formation layer and the sealing layer of the semiconductor package are well known, and those skilled in the art can use the resin composition and resin sheet of the present invention to manufacture the semiconductor package according to the well-known techniques.

[0422] (1) Step of laminating a temporary fixing film on a substrate;

[0423] (2) Step of temporarily fixing a semiconductor chip on the temporary fixing film;

[0424] (3) Step of forming a sealing layer on a semiconductor chip;

[0425] (4) Step of peeling the base material and the temporary fixing film from the semiconductor chip;

[0426] (5) Step of forming a rewiring formation layer as an insulating layer on the surface of the semiconductor chip after peeling the base material and the temporary fixing film; and

[0427] (6) Step of forming a rewiring layer as a conductor layer on the rewiring formation layer.

[0428] - Step (1) -

[0429] The material used for the base material is not particularly limited. Examples of the base material include semiconductor wafers such as silicon wafers; glass wafers; glass substrates; metal substrates such as copper, titanium, stainless steel, and cold-rolled steel sheets (SPCC); substrates in which epoxy resin or the like is infiltrated into glass fibers and heat-cured (e.g., FR-4 substrates); substrates formed of bismaleimide triazine resin (BT resin), etc.

[0430] The material of the temporary fixing film is not particularly limited as long as it can be peeled from the semiconductor chip in step (4) and can temporarily fix the semiconductor chip. Commercially available products can be used for the temporary fixing film. Examples of commercially available products include REVALPHA manufactured by Nitto Denko Corporation.

[0431] - Step (2) -

[0432] The temporary fixing of the semiconductor chip can be performed using known devices such as a flip chip bonder or a die bonder. The layout and the number of configurations of the semiconductor chips can be appropriately set according to the shape and size of the temporary fixing film, the production number of the target semiconductor package, etc. For example, they can be arranged in a matrix of multiple rows and multiple columns for temporary fixing.

[0433] - Step (3) -

[0434] The resin composition of the resin sheet of the present invention is laminated layer by layer on the semiconductor chip, or the resin composition of the present invention is coated on the semiconductor chip and cured (e.g., thermally cured) to form a sealing layer.

[0435] For example, the stacking of semiconductor chips and resin sheets can be carried out by heating and pressing the resin sheet to the semiconductor chip from the support body side after removing the protective film of the resin sheet. As a component for heating and pressing the resin sheet to the semiconductor chip (hereinafter also referred to as "heating and pressing component"), for example, a heated metal plate (SUS end plate, etc.) or a metal roller (SUS roller) etc. can be listed. It should be noted that the heating and pressing component is not directly pressed on the resin sheet, but preferably pressed through an elastic material such as heat-resistant rubber so that the resin sheet fully follows the surface unevenness of the semiconductor chip. The stacking of semiconductor chips and resin sheets can be implemented by vacuum lamination, and its stacking conditions are the same as the stacking conditions described in the manufacturing method for the printed wiring board, and the preferred range is also the same.

[0436] After lamination, the resin composition is thermally cured to form a sealing layer. The thermal curing conditions are the same as those described in the method for producing a printed wiring board.

[0437] The support of the resin sheet may be peeled off after laminating the resin sheet on the semiconductor chip and thermally curing it, or the support may be peeled off before laminating the resin sheet on the semiconductor chip.

[0438] When the resin composition of the present invention is applied to form a sealant layer, the application conditions are the same as those for forming the resin composition layer described in connection with the resin sheet of the present invention, and the preferred range is also the same.

[0439] -Process (4)-

[0440] The method of peeling the substrate and the temporary fixing film can be appropriately changed according to the material of the temporary fixing film, and examples thereof include a method of heating the temporary fixing film to foam (or expand) it and peeling it off, and a method of irradiating ultraviolet rays from the substrate side to reduce the adhesion of the temporary fixing film and peeling it off.

[0441] In the method of heating the temporary fixing film to make it foam (or expand) and peel it off, the heating conditions are usually 100 to 250°C and 1 to 90 seconds or 5 to 15 minutes. In the method of irradiating ultraviolet rays from the substrate side to reduce the adhesion of the temporary fixing film and peel it off, the irradiation amount of ultraviolet rays is usually 10 mJ / cm 2 ~1000mJ / cm 2 .

[0442] -Process (5)-

[0443] A rewiring forming layer (insulating layer of a rewiring board) is formed using the resin composition and the resin sheet of the present invention.

[0444] After forming the redistribution formation layer, in order to make an interlayer connection between the semiconductor chip and the conductor layer described later, vias can be formed on the redistribution formation layer. The vias can be formed according to the material of the redistribution formation layer by a known method.

[0445] - Process (6)-

[0446] Forming the conductor layer on the redistribution formation layer can be carried out in the same manner as process (V) described in the manufacturing method of a printed wiring board. It should be noted that processes (5) and (6) can be repeated to alternately stack (buildup) the conductor layer (redistribution layer) and the redistribution formation layer (insulating layer).

[0447] When manufacturing a semiconductor package, the following processes can be further carried out: (7) forming a solder resist layer on the conductor layer (redistribution layer); (8) forming bumps; (9) singulating a plurality of semiconductor packages into individual semiconductor packages. These processes can be carried out according to various methods well-known to those skilled in the art for manufacturing semiconductor packages.

[0448] By using the resin composition and resin sheet of the present invention that can bring a cured product with both good dielectric properties and good mechanical properties and crack resistance to form the redistribution formation layer (insulating layer), regardless of whether the semiconductor package is a Fan-In type package or a Fan-Out type package, a semiconductor package with extremely low transmission loss can be achieved without worrying about cracks. In one embodiment, the semiconductor package of the present invention is a Fan-Out type package. The resin composition and resin sheet of the present invention can be applied to both Fan-Out panel-level packaging (FOPLP) and Fan-Out wafer-level packaging (FOWLP). In one embodiment, the semiconductor package of the present invention is a Fan-Out panel-level packaging (FOPLP) or a Fan-Out wafer-level packaging (FOWLP).

[0449] [Semiconductor device]

[0450] The semiconductor device of the present invention includes a layer formed by the cured product of the resin composition layer of the present invention. The semiconductor device of the present invention can be manufactured using the circuit board of the present invention.

[0451] As semiconductor devices, for example, various semiconductor devices used in electrical products (such as computers, mobile phones, smartphones, tablet devices, wearable devices, digital cameras, medical instruments, and televisions, etc.) and transportation means (such as motorcycles, cars, trams, ships, and aircraft, etc.) can be cited.

[0452] Examples

[0453] Hereinafter, examples are shown to specifically illustrate the present invention. However, the present invention is not limited to the following examples. In the following description, "parts" and "%" representing amounts respectively refer to "parts by mass" and "% by mass" unless otherwise specified. The temperature conditions and pressure conditions without special designation are room temperature (25°C) and atmospheric pressure (1 atm).

[0454] (Synthesis Example 1: Synthesis of Resin A)

[0455] Dissolve 10 g of 4,4'-methylenebis(2,6-dimethylphenol) in 390 mL of tetrahydrofuran, add 15 g of 3-bromo-1-phenyl-1-propene, and cool to 0°C. Add 3.4 g of sodium hydride, and stir overnight at room temperature under a nitrogen atmosphere. Add water to the reaction mixture, remove tetrahydrofuran by concentration under reduced pressure, add dichloromethane, wash the organic layer with water and saturated brine, and dry with anhydrous sodium sulfate. After filtering and separating the desiccant, concentrate under reduced pressure to obtain 15 g of the target Resin A as white crystals. Resin A has the structure shown by the following formula.

[0456] [Chemical Formula 16]

[0457]

[0458] (Synthesis Example 2: Synthesis of Maleimide B)

[0459] Prepared a MEK solution (non-volatile component: 70% by mass) of Maleimide B (Mw / Mn = 1.81, t” = 1.47 (mainly 1, 2, or 3)) synthesized by the method described in Synthesis Example 1 of Publication No. 2020-500211 of the Technical Reports of the Japan Institute of Invention and Innovation. Maleimide B has the structure shown by the following formula.

[0460] [Chemical Formula 17]

[0461]

[0462] (Synthesis Example 3: Synthesis of Vinyl Resin C)

[0463] Put 3.0 moles (390.6 g) of divinylbenzene, 1.8 moles (229.4 g) of ethyl vinylbenzene, 10.2 moles (1066.3 g) of styrene, and 15.0 moles (1532.0 g) of n-propyl acetate into a 5.0 L reactor, add 600 millimoles of boron trifluoride diethyl ether complex at 70°C, and react for 4 hours. After terminating the polymerization solution with an aqueous sodium bicarbonate solution, wash the oil layer with pure water 3 times, and remove volatile components under reduced pressure at 60°C to recover the polymer. Weigh the obtained substance, and confirm that 896.7 g of Vinyl Resin C is obtained. The weight average molecular weight (Mw) of Vinyl Resin C is 41300.

[0464] (Examples 1 to 13, Comparative Examples 1 to 3)

[0465] (Preparation of Resin Varnish)

[0466] Weigh each component according to the parts by mass shown in Table 1, and further mix 10 parts of MEK and 2 parts of cyclohexanone, and uniformly disperse them using a high-speed rotary mixer to obtain a resin varnish.

[0467] [Table 1]

[0468]

[0469] It should be noted that the details of each component shown in Table 1 are as described below.

[0470] (A) Compound represented by formula (A-1)

[0471] · Resin A: Resin synthesized in Synthesis Example 1

[0472] (B) Maleimide resin

[0473] · MIR-3000-70MT: Toluene solution with a functional group equivalent of 275 and a non-volatile content of 70% by mass, manufactured by Nippon Kayaku Co., Ltd.

[0474] · Maleimide B: Substance synthesized in Synthesis Example 2

[0475] · SLK-6895-T90: Toluene solution with a functional group equivalent of 345 and a non-volatile content of 90% by mass, manufactured by Shin-Etsu Chemical Co., Ltd.

[0476] (C) Thermosetting resin

[0477] · LA-3018-50P: 1-Methoxy-2-propanol solution with a functional group equivalent of 151 and a non-volatile content of 50% by mass, manufactured by DIC Corporation

[0478] · HP-4032-SS: Functional group equivalent of 144, manufactured by DIC Corporation

[0479] · HPC-8000-65T: Toluene solution with a functional group equivalent of 223 and a non-volatile content of 62%, manufactured by DIC Corporation

[0480] · V-03: Toluene solution with a functional group equivalent of 216 and a non-volatile content of 50% by mass, manufactured by Nisshinbo Chemical Inc.

[0481] · DAD: Functional group equivalent of 161, manufactured by Nisshu Techno Fine Chemical Co., Ltd.

[0482] · Vinyl resin C: Toluene solution (non-volatile content 50%) of the substance synthesized in Synthesis Example 3

[0483] · OPE-2St: A toluene solution with a functional group equivalent of 590 and 65% by mass of non-volatile components, manufactured by Mitsubishi Gas Chemical Company

[0484] (D) Thermoplastic resin

[0485] · P2000: Styrene-butadiene elastomer, manufactured by Asahi Kasei Corporation

[0486] · PIAD200: Polyimide resin, a mixed solution of cyclohexanone, ethylene glycol dimethyl ether (dimethyl glycol), and methyl cyclohexane with 30% non-volatile components, manufactured by Arakawa Chemical Industries, Ltd.

[0487] · YX7553BH30: Phenoxy resin, a 1:1 solution of MEK and cyclohexanone with 30% by mass of non-volatile components, manufactured by Mitsubishi Chemical Corporation

[0488] (E) Inorganic filler

[0489] · SO-C2: Spherical silica surface-treated with an amine-based alkoxysilane compound ("KBM573" manufactured by Shin-Etsu Chemical Co., Ltd.), average particle size 0.5 μm, specific surface area 5.8 m 2 / g, manufactured by Admatechs Co., Ltd.

[0490] (F) Radical polymerization initiator

[0491] · PERHEXYL D: Manufactured by NOF Corporation

[0492] (G) Curing accelerator

[0493] · 1B2PZ: Manufactured by Shikoku Kasei Kogyo Co., Ltd.

[0494] <Test Example 1: Measurement of Dielectric Loss Tangent (Df)>

[0495] (1) Preparation of Resin Sheet A with a Resin Composition Layer Thickness of 40 μm

[0496] As a support, a polyethylene terephthalate film with a release layer ("AL5" manufactured by Lintec Corporation, thickness 38 μm) was prepared. On the release layer of this support, the varnish-like resin compositions obtained in the examples and comparative examples were uniformly coated so that the thickness of the dried resin composition layer would be 40 μm. Then, the resin composition was dried at 80°C to 100°C (average 90°C) for 2 minutes to obtain resin sheet A containing the support and the resin composition layer.

[0497] (2) Preparation of Cured Product

[0498] The obtained resin sheet A was cured in an oven at 190 °C for 90 minutes. The resin sheet A was taken out of the oven, and the support was peeled off from the taken-out resin sheet A, whereby a cured product of the resin composition layer was obtained.

[0499] (3) Measurement of dielectric loss tangent (Df)

[0500] The cured product was cut into pieces with a length of 80 mm and a width of 2 mm. Using "HP8362B" manufactured by Agilent Technologies, the value of the dielectric loss tangent (Df value) was measured by the resonant cavity perturbation method at a measurement frequency of 5.8 GHz and measurement temperatures of 23 °C and 90 °C. The measurement was carried out using 2 test pieces, and the average value was calculated.

[0501] <Test Example 2: Measurement of elongation at break>

[0502] The tensile strength of the cured product obtained in Test Example 1(2) was measured using a tensile testing machine "RTC-1250A" manufactured by Orientec, and the breaking strength and elongation at break at 23 °C were measured. The measurement was carried out in accordance with JIS K 7127. Five measurements were carried out, and the average value of the top 3 values from largest to smallest was calculated.

[0503] <Test Example 3: Evaluation of crack resistance>

[0504] (1) Lamination of resin sheets

[0505] An inner layer substrate (Resonac's "MCL-E700G", the thickness of the conductor layer is 35 μm, the total thickness is 0.4 mm, and the residual copper rate is 40%) having circuit conductors (copper) formed by a wiring pattern of L / S = 8 μm / 8 μm on both sides was prepared. Resin sheets were laminated on both sides of the inner layer substrate in such a manner that the resin composition layer was in contact with the inner layer substrate. The lamination was carried out as follows: using a vacuum pressure laminator ("MVLP-500" manufactured by Meiki Seisakusho), after vacuum suction at 120 °C for 30 seconds, under the conditions of a temperature of 120 °C and a pressure of 7.0 kg / cm 2 , pressing was carried out through a heat-resistant rubber from the support for 30 seconds. Then, under atmospheric pressure, using a SUS end plate, pressing was carried out under the conditions of a temperature of 120 °C and a pressure of 5.5 kg / cm 2 for 60 seconds.

[0506] (2) Thermal curing of the resin composition layer

[0507] Heat at 130°C for 30 minutes, then heat at 170°C for 30 minutes to thermally cure the resin composition layer, obtaining an insulating layer as a cured layer formed from the cured product of the resin composition. Then, peel off the support to obtain a sample substrate having a layer structure of insulating layer / inner layer substrate / insulating layer.

[0508] (3) Roughening treatment

[0509] Perform roughening treatment on the insulating layer of the sample substrate. Specifically, immerse the sample substrate in Swelling Dip Securiganth P manufactured by Atotech Japan Co., Ltd. as a swelling liquid at 60°C for 10 minutes. Then, immerse it in Concentrate Compact P (KMnO 4 : 60 g / L, NaOH: 40 g / L aqueous solution) manufactured by Atotech Japan Co., Ltd. as a roughening liquid at 80°C for 20 minutes. Finally, immerse it in Reduction solution Securiganth P manufactured by Atotech Japan Co., Ltd. as a neutralizing liquid at 40°C for 5 minutes.

[0510] (4) Evaluation of cracks

[0511] Observe the part on the L / S pattern of the inner layer substrate on the surface of the insulating layer after the roughening treatment. Confirm whether cracks (cracks) are generated on the surface along the pattern shapes of 100 inner layer substrates, and calculate the proportion of the number of parts on the pattern where no cracks are generated. Calculate this proportion as the "yield rate". In addition, the calculated yield rate was scored according to the following criteria.

[0512] 1 point: 0% or more and less than 20%.

[0513] 2 points: 20% or more and less than 40%.

[0514] 3 points: 40% or more and less than 60%.

[0515] 4 points: 60% or more and less than 80%.

[0516] 5 points: 80% or more.

[0517] Evaluate 4 points or more as ◎, 3 points as "○", and 2 points or less as "×".

Claims

1. A resin composition comprising the following components (A), (B) and (C), (A) A compound represented by the following formula (A-1): [Chemical formula 1] In formula (A-1), X represents a divalent group represented by the following formula (A-2) or a divalent group represented by the following formula (A-3), [Chemical formula 2] In formula (A-2), R 11 and R 12 Each independently represents a divalent aromatic group which may have a substituent, L 11 Each independently represents a single bond, or a divalent linking group optionally having a substituent, R 11 and L 11 can be combined to form a ring, a represents a number in the range of 0 to 5, [Chemical formula 3] In formula (A-3), R 13 and R 14 Each independently represents a divalent aromatic group which may have a substituent, L 12 represents a group represented by formula (A-4), b and c each independently represent a number in the range of 0 to 5, [Chemical formula 4] In formula (A-4), R 15 and R 16 Each independently represents a divalent aromatic group which may have a substituent, L 13 Each independently represents a single bond, or a divalent linking group optionally having a substituent, R 15 and L 13 can be combined to form a ring, d represents a number ranging from 0 to 5; (B) maleimide resin; (C) Thermosetting resins, excluding maleimide resins.

2. The resin composition according to claim 1, wherein R in formula (A-2) and formula (A-3) 11 , R 12 , R 13 and R 14 Each independently represents a phenylene group which may have a substituent or a naphthylene group which may have a substituent.

3. The resin composition according to claim 1, wherein R in formula (A-4) 15 and R 16 Each independently represents a phenylene group which may have a substituent or a naphthylene group which may have a substituent.

4. The resin composition according to claim 1, wherein L in formula (A-2) 11 Each independently represents a single bond, a divalent aliphatic group which may have a substituent, an oxygen atom, a divalent aromatic group which may have a substituent, a carbonyl group, and a sulfonyl group.

5. The resin composition according to claim 1, wherein L in formula (A-2) 11 Each independently represents a single bond, a divalent aliphatic group which may have a substituent, an oxygen atom, a phenylene group, a fluorenylene group, a carbonyl group or a sulfonyl group.

6. The resin composition according to claim 1, wherein X in formula (A-1) is a group represented by the following formula (A-5), [Chemical formula 5] In formula (A-5), Rs each independently represents a substituent, L 21 Each independently represents a single bond, a divalent aliphatic group optionally having a substituent, an oxygen atom, a phenylene group, a fluorenylene group, a carbonyl group or a sulfonyl group, wherein when L 21 When L is a divalent aliphatic group which may have a substituent, 21 It can combine with the benzene ring on the left to form a ring. n1 and n2 each independently represent a number in the range of 0 to 4, m represents a number in the range of 0 to 5, "*" indicates a connection key.

7. The resin composition according to claim 1, wherein When the resin component in the resin composition is 100 mass %, content of the component (A) is 2 mass % or more and 12 mass % or less.

8. The resin composition according to claim 1, wherein When the resin component in the resin composition is 100 mass %, content of the component (B) is 20 mass % or more and 75 mass % or less.

9. The resin composition according to any one of claims 1 to 8, wherein The component (C) contains one or more selected from the group consisting of epoxy resins, phenol resins, and terminal double-bond resins.

10. The resin composition according to claim 1, wherein When the resin component in the resin composition is 100 mass %, content of the component (C) is 10 mass % or more and 50 mass % or less.

11. The resin composition according to claim 1, wherein It further contains (D) a thermoplastic resin.

12. The resin composition according to claim 1, wherein It further contains (E) an inorganic filler.

13. The resin composition according to claim 12, wherein When the nonvolatile matter in the resin composition is 100% by mass, the content of the component (E) is 50% by mass or more. 14 . The resin composition according to claim 1 , which is used for an insulating layer of a circuit board. 15 . A cured product, which is a cured product of the resin composition according to claim 1 . 16 . A resin sheet comprising a support and a layer of the resin composition according to claim 1 provided on the support.

17. The resin sheet according to claim 16, wherein The support is a thermoplastic resin film or a metal foil. 18 . A circuit board comprising an insulating layer formed from a cured product of the resin composition according to claim 1 .

19. A semiconductor device comprising the circuit substrate according to claim 18.

Images